We plan to DIY and upgrade, and our exit strategy will depend on what rents look like in four years as to whether we hold or BRRR.

@Dan Lucchesi - Here is a CSS Decision Diagram flowchart intended to bring together all the various questions when assessing the benefits of a CSS (via a professional or DIY).

@Saravanan VaradanYou are probably talking about DIY software-based cost seg.

Regarding remote managing, in our 24 years of experience, dealing with hundreds of investors, what we've had to bail DIY Remote Investors out of is mostly Class C properties with some Class B.So, in our opinion, one can remote manage a Class A property fairly easily if you are organized.Class B requires more organization and knowledge, to avoid tenants taking advantage of you.Class C should NOT be done DIY - hire a PMC!

Most land somewhere in the middle.If you have experience as a DIY landlord, what has been most challenging about it?

They are only a software provider for DIY rental property owners.

Boston Housing Authority - Boston Housing Authority (click on "For Landlords" tab)If you're serious about being a DIY landlord, you're going to have to invest MORE time into research than just posting here for help.Go spend 30 minutes on their website and then ask more specific questions for clarification.

I've begun volunteering with Habitat for Humanity to gain more confidence in DIY improvements. 

Also, I would be very concerned with thinking you can DIY your first renovation.

Run  some 220V wiring in pvc underground (licensed electrician) to power a good pump if you have space/amperage reserve in your electrical panel. 220V requires less current to run than a 120V for the same power, so it's more efficient.This guy has a lot of good videos on diy yard drainage systems.