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. 

After trial in April 2023 he appealed the decree and we settled in Supreme Court that the LLC, the physical rental property, and the mortgage would be my responsibility.  

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. 

Yes, you're missing the underlying appreciation of the house, the value of storing money in a physical asset versus an alternative and capex costs.