Over 20 years ago when I started a hard money fund a “potential” client asked me to evaluate a potential acquisition for him, which I did.  

What I’d recommend is mapping out all the possible scenarios and evaluating what works best for your situation.

You could also possibly partner with a relative who knows / trusts you to make up for any shortcomings you may have.After that, presuming you have good credit, you can go to a mortgage broker and they will evaluate your credit and financial "worthiness" against their requirements for their lenders to lend to you.  

Your perception, where you grew up and how, are going to determine how you evaluate a neighborhood. 

Just a heads-up—bonus depreciation can be claimed up to 60% for 2024, and it will drop down to 40% in 2025, so that’s something to keep in mind as you evaluate your options.I’m not endorsing any particular company, and I don’t receive referral fees for recommending the one I used.

I am trying to evaluate the benefits & risks on purchasing a 2-4 family or a single-family home and convert/build an ADU.

Once you have an idea of what you can do you want to evaluate the site and the market for competition.

I think you need to take a look at what you expect from a PM and evaluate them from that lens.

Outside of the kry metrics one needs to evaluate when investigating any market, I also created a list of priorities and nice-to-haves.

Makes sense though - it's like pricing, it's very easy to price units in a condo building since they are all so similiar vs a custom home which can be very difficult to evaluate.