Sell, get the tax savings while you can.

A hybrid approach could work best: start with a cash-flowing Texas rental while saving for a Long Island house hack later.

I know the "survive till 25" crowd was banking on interest rates going down to the 4's or low 5's next year and that was going to save these deals.

Congrats and knock out that extra debt you accumulated so you can save up for STR #2!

The positives are from the buyers prospective1- the ability to buy a property with little down payment2- the ability to obtain financing at below market rate3 -not needing to qualify for convention/institutional financing4- not having another debt on your PFS5 - not needing to pay points and other fees to obtain a new mortgage The positives for the seller are 1- can possibly sell a property in which they have negative equity without bringing cash to the closing table2 -expand the pool of potential buyers 3 -possibly obtain a higher price/ quicker sale 4 - can utilize a wrap to potentially earn the “differential” on interest rate 5 -May be able to save the Realtors commissionAll this being established, here’s the BIG question:  Can a subject to transaction be done where both parties are reasonably protected?  

It’ll save you headaches later if she tries to escalate things.Document Everything: Take pictures, write down the history of your interactions etcOffer a Transition Plan: Just like my client, I’d recomend offering her a temporary storage option nearby, or even a small rent discount, to show you’re not trying to kick her out - just keeping the property safe and up to code.

They also have a good understanding of different lenders' appetites, and thus can save time by filtering out lenders that won't be competitive. 

Dave’s team saved me from all that.

Are there certain red flags that have saved you from a bad lease before?

I have equity in my CO rental; I don’t have a large enough sum saved up for a down payment yet so I’m wondering if a HELOC would be an option on my CO property.