For the multi-family, lenders typically count about 75% of projected rental income toward your debt-to-income ratio, which should help if the property is cash-flowing.

Testing the entire BRRRR process to see if it's the right strategy for me long-term.building equity through rehab and build out will be best achieved with a lower priced cash purchase---typically wholesale. or word of mouth. depends on the region though. lots of ways to hunt for good BRRRR candidates, but hunting on the MLS typically wont get you low enough prices to make sense....My brother-in-law, who owns a landscaping company in Lee’s Summit, works with a lot of local builders and has been a huge help...This sounds like a great resource for finding subs that will do the work for you independently. most subs can do other types of work as well.If you’ve worked with trustworthy contractors or subcontractors in the Jackson County/MO area (especially those familiar with investment properties), I’d love your recommendations.

I've done a few so I'm typically offered 90% LTC.

That's a typical scenario and could cost you $10,000 - $15,000 so that would be a good starting point for your reserve.But there's more!

Also, not sure what relationship you have established with your property manager but typically people hire managers to take care of this part and be tenant-facing.  

You'll have access to owner occupied loan products, therefore saving on your down payment, typically 3-5% compared to 20-25% for non owner occupied properties.

Typically, we conduct background checks on only the individuals who are responsible for the lease (primary resident) and/or cosigners.

As a SFR investor for over 15 years I have been wrestling with this question in the past, because it feels like you should upgrade to "bigger".I know for sure that I would not enjoy the ownership experience that comes with a small 4F, because in Milwaukee that typically also means lower income tenants. 

Personally I wouldn't feel comfortable trying to wholesale a relatives $1M home knowing that I am breaking the law if I cross over into doing anything that can be considered representing them in the transaction, and knowing it will only be marketed to people who buy properties wholesale (typically investors who don't want to pay retail prices), instead of the majority of retail buyers active in the market who are typcially willing to pay more. 

It has to be something the individual wants, and let's face it, that isn't your typical BP investor.