Generally best bet is to be able to do significant portfolios at a time and try to bundle at least 8-10 of these in one blanket loan

It was inspected as a duplex, and I'd bet it'll be appraised as a duplex as well (basically removing the oven gives the appraiser plausible deniability), which could create value issues and impact your DTI if you need to use rental income to qualify. 

I bet they are pounding on this guy hard to. 

I bet Maine is GORGEOUS!!

I'm in the union on long island so I have a decent W2 job to help get started, I think a house hack would be my best bet starting out but, what do you guys think?

Respectfully,Zach The best bet is likely to create a new LLC that lays things out in a straightforward but legally strong and standard operating agreement, etc. - LLC doc sets are fairly cheap and easy to create these days (with limited assistance from lawyers) and its much much better to have that cover bases on arrangements like this - it will also fit nicely with financing options - whether you take on debt from a lender in a co-equity situation like your first plan (refinance loan to LLC post rehab?)

If you can run a successful arbitrage business you can make a lot of money, and if you hedge your bets and put that money back into owning more assets then why not?

If you’re just saying the survey cost of getting the existing building layout documented is too much, you might be able to get creative and avoid the costs, but it’s not a great bet to make. 

Often times inspectors overlooked them as they are very small and minor but as you can probably already tell, they are extremely important and prevent water intrusion.Your best bet would be to contact a very reputable Siding/roofing contractor and have them go through the entire property and put in the proper drippage flashings seals and caulking necessary and have them insure the work. 

I am betting that those with the biggest regrets are those that bought at the wrong time expecting COVID level occupancy was normal and those that didn't take the time to learn what it takes to run a successful STR.