Bitch. At 48 I am middle aged.

This is going to sound a little harsh, but...

If you don't grow some balls, get out of your comfort zone, and be a little outgoing/aggressive then you will continue to be alone. You will get shot down and sometimes you will get shot down with great flair and drama. That's a given. Accept it and move on. You will learn to ignore the bullshit and not fucking care what anyone thinks about you. It is at this point that the tables turn and you have to start beating the women off with a stick.

The meek may inherit the earth but they won't be getting laid. Weak-sauce is one sure fire way to dry up vagina like the Sahara. Fortune favors the bold and so do the women.

I'm not sure is 34 is "middle-aged", but it's certainly old enough, I feel like I should be over this.

It is mate. Stop pussy footing around it, you sound like a woman.

I'm in the process of starting my own marketing firm

Lol, keep pursuing that dream and chase the dragon mate, you might be right, you're not middle age, and still a child

When it comes to women, though... I'm just lost.

Most men are, unless you had a lot of sisters or a lot of cheer-friends - you were segregated from women for most of your life.

but it's honestly nice just spending time with someone you can connect with, and I just straight up need more practice.

Women are not your friends, you need to train your brain out of this shit and find actual friends. Also, you're not looking for "practice" but rather a woman that makes you feel like a man - you have just conditioned yourself to hate yourself for having male wants and desires. For that there's unfortunately only 1 solution: whores. They are literally paid to make you feel like a man - even if you are the most passive, fat slob around. As you understand what a woman can make you feel and what regular women actually give you - you will be much more motivated to lift, find some game and stand up for yourself with women. And that's when regular women actually start acting like slutty little sex kittens instead of princesses you need to convince into touching your peepee.

It's hard not to feel like kind of a loser when you aren't achieving ANY level of success with women.

Be glad you're not some marketing chump that spent all his time and energy building up a to a level where hotties give him attention and then end up paying for a blowie with $5000 Belenciaga's - that's what's actually hard - to have all the leverage but be blind to it and still live off scraps.

I relocated about 6 months ago, and I'm helping take care of my dad as well, and since I don't have any friends in the area

See, that's actually a flex. Sorry to hear that man. But friends are easy - just be kind and cordial and hang out with people that share your interest. Hopefully your only interest isn't Gary V - because that sucks for you, those people are horrible.

infecting your confidence in EVERYTHING if you don't find some way to address it

Nah, it's not, but you can't see it right now. But mark my words: lack of confidence is a earworm - you have felt powerless in the past and now your brain is trying to fix it. How does a brain fix problems: It mixes and matches events with potential causes, to create a predictable model that helps it navigate the world and avoid other such powerlessness moments. Sucks that this makes people avoidant of the issues that they don't have power around - therefore guaranteeing they will never gain proficiency and power in those areas. When it won't be women, yur brain will still look to other reasons why you are powerless. The only solution is to become powerful, to gain the love and respect of others. To help without wanting and to care without desiring. But that's later in your life. After you fix whatever Andrew Tate, 3 hour work week, digital hustle mindset you have going on now.

I'm just at a loss on what EXACTLY I need to be doing.

Whores and kindness - preferably not in the same setting. Because a whore will take you for broke if you don't stand your ground and think she is a scared little woman that is a victim.

You are making women the prize. They are not, you are. Focus on your success, women fill also focus on your success. Their attention will follow.