Starting out, have potential leverage, need advice

[Kenneth B.]

Hey everyone! I'm looking for a bit of advice or guidance for starting out on my REI journey.

I have a second home free and clear that I own about two hours away from where I live. I've rented it out previously to some acquaintances just to have people in the house before I really decided what I wanted to do with the house. This was before I started learning about REI. The house is now vacant, needs a bit of cosmetic work on the inside, driveway is beatup, and the small one-stall garage roof needs to be replaced. All major appliances including AC/Furnace, w + d, kitchen appliances, etc are relatively new. Roof is in good shape.

I'm at a crossroads as to what I should do with the house. It's pretty far away for me to self manage, as I have a primary home with family, job, etc. But I'm also wanting to invest in LTRs to build a portfolio and perhaps start with investments closer to where I live. I'm open to suggestions as far as looking into a HELOC on the second home or even selling it if that's a good option. My thought process on the 2nd home HELOC is to update the 2nd house, and maybe use the rest for down payments on other potential rentals. I'd of course have to get tenants in there. Is this a good option? I'm also a bit low on cash, personally. I'm worried that if I get a HELOC and start using it, payments will come due and I don't have any incoming rents yet as I don't have tenants. Should I get tenants in before doing potential updates? Should I just sell the house and use that as down payments on potential LTRs? I'd hate to take a tax hit if I don't have any lined up.

There's a lot to process here but I'm starting to get into analysis paralysis and need to take the first step.  Let me know what you think.  Thank you!