What might work well on one street could be a completely different story just a block or two away.

You have to walk these properties, understand where the hidden costs are outside of the spreadsheets, and understand the geographic appreciation trend and migration and population as well, none of which will be in the questions you are asking. 

It's less risky for you if it doesn't rent well and it's more profitable for him (most likely) without the headache.  

You've done well with having options, now just need to decide and get on the same page. 

By the way - for the same reason the 1st position lien holder will be uneasy with 100% CLTV, as a buyer I would be uneasy with it as well.

Well Giacomo, Sometimes you are the football and sometimes you are the foot.

I invest in Richmond as well, through house-hacking and BRRRRs primarily!

I am hoping to make connections to learn more about this market, which neighborhoods to focus on, as well as learn some pro tips as I begin my investing journey.To note, I have begun the loan pre-approval process and have a dedicated agent that is eager to find me a great property. 

My situation currently is I have 1 SFH rental that is owned by my LLC and doing well, and also I'm doing a live-in flip on my primary residence.

@Gary Abrams A cloud based solution would work really well in your scenario of having other family logging in and helping with management.