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?

I bet they are pounding on this guy hard to. 

I bet Maine is GORGEOUS!!

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 have a reliable trust-worthy agent who has connections in most markets you don't need a PM. 

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. 

We just found her through UpWork.com which is probably your best bet for quality VAs. 

Even without a track record these individuals presumably know you as an upstanding and trustworthy guy and this means you only have to sell them on the merits of the real estate.

These days I bet because no one builds them they probably cost more than a traditional.