The second one needed a full roof.

People are often lax when it comes to their revolving credit but not with the roof over their head.

Its ALL about doing the reno correctly, Roof, and furnace/HW tank if older then 10yearsish, replace, all new cosmetics including LVP through entire, ect.

Sloped, flat, rocky?

or “Is it legal to build a treehouse on a duplex roof?”

I’m seeing rents a flat or slightly down in my market and that is because then went up so quickly.

I also flatly reject the notion that you don't want to work with any of the bottom 90% of the agents.

Anything above that needs to be justified - roof replacement, parking lot repaving, etc. 

The town owns the lake, so they get a little more leeway there and people who own $4 million homes don't want to see mud flats, so the lake stays full most of the time. 

I would suggest just that, house hack a 4plex for cash flow, and save for your second creative finance deal and grow from there.The idea here is you should be paying zero for your roof (or close to) before buying a second property.