We occasionally take out some profits for fun money. 

Or ,perhaps , can I rent one rooms to someone or do Air Bnb  occasionally, while still living there?

Full disclosure - I did work for him part-time and will occasionally help him with simpler returns when he gets slammed this time of year - but I don’t get compensated or anything, just a genuine recommendation for someone I’ve seen save people tons of money.If you want more info you can message me or just Google LTR Financial Services.

I am interested in single family and/or small multi family initially with a buy/improve/manage strategy for the medium term - (7-10 years) with an occasional flip when/if it makes sense.

I am free to climb on most weekdays after 5pm, and occasionally on weekends.

I'd really prefer to be able to ask and answer questions or send referrals privately without having to necessarily be connected to that person as a colleague.Case in point: occasionally I receive colleague requests with no message attached to it.

I have a few folks who occasionally send me leads on run-down houses in my mid-sized market. 

Occasionally you will need a new bathroom and/or kitchen so you will need to be setting some aside for that.You mentioned good HOA management.

I actually got my license to list an occasional rehab and to get MLS access, and it has been very helpful.

They stayed warm due to generating lots of heat internally and only heating the portions of the house being used {i.e. you would not heat the dining room or salon during the night}.With older properties we usually lay-out a plan to improve the building envelope first through air sealing (getting rid of drafts and convection within the wall cavities) and, where possible, insulation {not always straight forward ... many old brick buildings have limited insulation options due to the brick requiring heat transfer from inside to drive moisture from the brick}.Around here it is not uncommon to find an old mansion converted to multiple units - or the occasional purpose-built multi-unit - where the operating costs are 70 - 80% of the revenue and heating comprises 20 - 25% of the operating costs.