Does again with multiple houses will give you $20k+/month.  

I would target a 2.5x equity multiple and 8% cash on cash return, but I would focus mainly on the operators and try to figure out if I believe in the team and vision, and really try to understand if I trust them or not.

When you go to sell, Montvale requires a certificate of occupancy so this issue has to be resolved in advance of a sale.Although I am not a lender, I assume you will not be approved for an owner-occupied mortgage on 5-units if it is a legal 4-unit without some type of mortgage fraud whether in reported rents, units, or another legal document or representation (very very large issue from a legal perspective with multiple arrests in the last year for anyone playing fast and loose).As far as the DCA, I would recommend coordinating your work with the city with the DCA.

I hadn’t thought about the risk of expanding my portfolio by having multiple properties over leveraged, although that seems to be a growth strategy that many use,  I’m not sure it’s one I’m comfortable with.  

I’ve owned multiple mobile home parks and would never try to rent them out for the reason mentioned above.

I use Wisconsin Legal Blank forms, they are inexpensive and court-tested.

It’s a lot to keep track of, especially when researching multiple markets.Would greatly appreciate any advice/insights from experienced investors who've navigated these challenges :- How do you approach understanding and evaluating short-term rental regulations when considering a new market?

The end goal is to have a piece of land with multiple houses: one for my growing family but also a home for my mother in law.My mother in law has agreed to foot the money on a new property/land up front and when ready we can buy land from her to build/develop etc. 

. 😉  also, a lot of the 3/4 size Arcade1 games have multiple games loaded on them.Yea so I have a variety.  

I actually asked in writing multiple times to verify it was a triplex as that is what I was wanting to buy.