I've tried a few softwares - RentRedi, Innago, and Baselane to name a few and have chosen to stick with Baselane.

My most gracious analysis would be this (and this is just me): (1) I think the owner is a very kind man - I’ve talked with him personally.

So having a joint account makes sense BUT my team and I will also have separate deals outside of this partnership with this other person.

In other words, the person with the most toys, wins... not the person who paid the least amount of tax.

We took the depreciation on our personal tax return in 2022.

We are shooting for 3x income, but might settle for as low as 2x, if the person seems like a good candidate.

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.