So I thought I’d see if they’d like me to knock a few bucks off their rent and I’ll take the 3rd floor Since it’s located downtown and has 3 of the four walls as windows looking out (ie great views), it seems like it would be great for shared office space (think, “weWork”).

It says it has vinyl windows but its wood windows from 1926.

Not paying rent because a window doesn't work properly is not reasonable at all.

Some of the jobs looking to hire out for include replacing back deck, replace a ton of drywall, electrical, 2 bathrooms, couple windows, and some duct work. 

Brian would fund some renovations on the property, new subfloor and LVP, paint, adding some windows, updating the AC, and one by one we would renovate and lease each unit from him.

The radiant electric heat, from what I've been told and researched, could actually be fairly efficient, especially because the house is well insulated with newer windows. 

lots of rehab, pretty much new interior and windows What was the outcome?

Although most was, none of the windows were repaired and a few smaller jobs were not repaired (fixing the front railing). 

I put about $25K into the last place I got to get it in good shape (had to gut the bathroom to the studs and put in new kitchen cabinets and countertops, 4 new windows and drywall the ceiling in three large rooms...plus a few other things) and it currently rents for $1350. 

A lot of investors see that 5-7 year time frame as the optimal window to move on from a property because it is often around the time that many capital expenditure items start needing to be replaced again which begins erasing built up cash flow.