Over the years every single time I went over his house to hang out we would talk about money, investing and the future we were building.

We've had one cabin that has failed to pay a single assessment since the inception of the HOA one year ago and has wracked up $1750 in late fees. 

We are looking for low maintenance (so primarily new construction or >2000 and well maintained/rennovated) single family homes.

There's other items such as this where it may be helpful to talk to a CPA/EA for a little tax planning, especially since you'll likely get caught up in the passive activity loss limitations if taking bonus on a single rental property as I often see.It's also useful to mention that even if you do the cost seg study (I'm assuming you're doing one to be talking about this), you'll still benefit from accelerated depreciation in the form of shorter useful lives on the assets where you received bonus from.

I am considering in investing in Single-Family/Multi-Family mid-term and long-term rentals.

My wife and I own a single-family home in a top school district.

Quote from @Michael Moya: Hi Bigger Pocket Community - Looking for some insights and advice on loan options for single family homes under $120K.

The area’s limited number of apartment buildings means that many renters prefer single-family properties, creating steady demand for these homes.Happy to chat further if needed.

Alternatively, if I can find a lower cost single fam home where I can cash out 100% of my investment I would do that but those have been harder to find recently. 

Once you take over a property as an owner occupant, if it is a single family or condo you can live in it for 1 year and that automatically exempts your unit from rent control.