He knows how to do almost everything, but due to his pace I use him for mainly handyman work(toilets, fixtures, tuckpoint, wood work, switches/covers, etc) He has done minor HVAC and electrical for me as well, but..

Most lenders are going to want to see a few big things from the ownership group. 1) The borrower will be the enitity (LLC, S-Corp, etc) and any owner with usually 20% or more of ownership in the entity will be expected to guaranty the loan, 2) We'll want to see some experience doing similar projects from at least one of the main owners, 3) We'll want to see bank statements showing liquidity enough to cover the intial cash injection (down payment), the closing cost, and some cash in reserve.

If you look at what they have avaliiable on the website its mainly desert lots.

If you are NOT running a trade or business - 1099s are not required.The main reason why you WANT to be "running a rental trade or business" is your eligibility to claim business overhead deductions, such as marketing, education, technology, and so on.

I was looking at him mainly because he is in my area but I had a lot of questions. 

IDEALLY, we would like to find a property that has or is capable of being converted into a “mother in law”, “ADU”, “Casita”, or any other separate living quarters in which we could rent out the main portion to a tenant (short term or long term) and then use the separate space as our own for when we come and go with business.

Building a Phase 1-5 messaging campaign is the easy part.I'd recommend you build this yourself, so you can see what's working and what's not, and improve it over time with added features, automations, and complexity.

Your tenant's friend will probably just draw it from whatever nearby circuit thay can tap into most easily.....So running a new 14/2 cable from the main panel will probably not be easy unless it is really close.

The owner is living in the ADU and renting out both levels of the main house on AirBnb.

Sell: The home is stunning, with features like a 2-story wall of windows and a central, convenient location.