@Joshua Martin,If there’s a chance you’ll sell next year, a HELOC might be the better move since it typically has lower upfront costs compared to a cash-out refi.

Imagine you make $100k and you are affected by 3 tax brackets.0-33k =-33K 0%33,001-66k 10%66,001 - 100k 20%You can take $100k in deductions this year and pay zero taxes, for one year and then $10,100 for for 2 years  ($20,200 total)You can take 67k in deductions this year and pay zero taxes for a year, take 33k the second year and pay $6,800 year two and $10,100 year 3. ($16,900 total)You can take 33k each year and pay $3,300 in taxes all 3 years. ($9,900 total)Obviously this is simplified but unless you expect to make much less and be in a lower tax bracket in the future those deductions could come in handy.

I feel like a GC would have been able to get me better deals with contractors while taking away the headache of not having to babysit contractors through this 1.5 year ordeal.

After being a fan of the area for a number of years and analyzing countless properties, I've actively been looking to expand there myself.I sent you a message.

If I believe I can generate enough profit this year and navigate any potential inspections next year, I’d be comfortable moving forward—using the income earned to cover any necessary upgrades.An alternative exit strategy is to document the financial performance and sell the property as-is, highlighting its strong short-term rental income.Think through your next five moves, from best to worst-case scenarios, and make a decision that aligns with your goals. 

We have a checkbook LLC account with Titan bank that we setup from our SDIRA company and haven't had any issues for the last year from any transactions.

My wife and I are about to put our WI lakehouse out as a STR this year.

My thoughts: don't get set on just one trend since your goal is to purchase in 2026, as we've all experienced, a lot can happen in a year.  

The only way I KNEW it was a good deal is I had been researching two areas for about a year. 

I signed up last year and I'm just now started to take my investment plan seriously.