Would it be helpful to you as a landlord have have not only the day to day automated but also have guidelines and quick access to local regulations (where there is constant change) in your assets markets to help you stay compliant and avoid potential lawsuits/fines?  

We plan to hold this asset for 3-5 years.

Are you only doing private money are you doing asset based/traditional as well? 

Sober living is one of the hardest management assets out there.

It'll be nice to use just one software, but I think it's better to use both Buildium and QuickBooks if you want to keep track of everything, likes your assets. 

I did a background check and was able to look up his many properties across all states so I really don't have concerns he doesn't have any assets. 

Valuation of the asset condition is even more important than calculating returns because your calculation of returns comes after asset condition valuation. 

2) Also, is it allowed for proceeds of both sales to be used as down payment towards 1 single asset?

If you're both 50/50 in each asset, why not create a partnership now, and contribute both assets to the partnership; where you will be 50/50 owners.

I also have a digital agency business and am acquiring a new SMB in-home service.