Now, I’m curious about real estate investing.I have some experience flipping a couple of houses, and although I have a ton of flaws, one of my strengths is being resourceful and assembling amazing teams—I’m always looking for people better than me at what they do— what seems to be a good fit for real estate.

There is a catch - the couple wants to 1031 the funds into their sons next larger project which is TBD.

We haven't bought anything in the past couple of years locally because the value proposition compared to what we already own just isn't there.  

A couple of years ago there was an excellent long article on BP about all the things to look for and ask when interviewing property managers. 

Right after I closed on that one the insurance company demanded I make a couple thousand dollars of repairs.

For example, I've had a couple of 3+ bedrooms sit for a longer period of time because they only had one parking space available (and no on-street options nearby).

.), I'd recommend that the residential units fully cash flow the loan as my experience is that mixed use properties are tougher to finance as most lenders tend to prefer one or the other and something in the middle gets more difficult.For example, and granted I don't know anything about the area/neighborhood, I would expect this property (https://www.realtor.com/realestateandhomes-detail/111-NW-Har...) to be easier to finance than the mixed-use property you mentioned. 

Consider house hacking when rates and prices are a little more balanced with reality.I would prefer a duplex/triplex but I know getting into a single family home and renting out the rooms is more accessible .

Just an extra couple of clicks to do.

., preferably with a great outdoor space.