It is a bit of a gamble, but personally, I always get my own bids from people I will hire and either take a credit on price or have title issue the checks directly to those contractors to get work done as soon as I close.  

I would vet them intensely and make sure the lease is personally guaranteed. 

James has time and time again always posted extremely helpful information on every post, he would be a great person to connect with. 

Response to #1: Some lenders allow for layered entities while others want warm bodies/natural persons to be direct managers.

Haven't personally used either but they are both on my radar.

As long as the person hasn't used RAFT in the recent past then RAFT will cover up to $7,000 for first, last and security as long as they qualify.

If you can't keep control of your personal finances, you are highly unlikely to succeed in real estate investing.

I invested in 7 syndication funds in 2023 as a limited partner with the expectation that I would generate first year losses from cost segregation that I could use to offset my gains on my personal real estate investments (self storage). 

No there is still one person living there right now. 

Typically that's the roll of a business broker vs real estate agent, although sometimes one person does both.