I'm looking to start off in areas with lower costs coming in, preferably under $100k single families but definitely under $200k. 

Hello, I’m mainly interested in single family and want to stay in my local area (Tucson Az) mostly because I’m here and I know this local market fairly well.

Price of entry is high, rent is super low. 

Site cleaning may be the single most underfunded line item on construction budgets which often leads to dangerous work sites.

It's amazing how people on these voting committees single in on issues that should not stand in the way of community progress like landscaping, parking, and dog parks.

It seems like your ROI is basically the same in each option, but you are taking on a much bigger project to convert a single family to a four-family.So basic calculations, since we don't have a full financial picture, i.e. what does financing of each look like?  

Super accurate.

I currently have a 30-yr fixed rate mortgage on a single family home that is my primary residence.

If you are single or married without kids and an understanding spouse.

Some HOA's are super strict (especially in neighborhoods built in 2010 and newer) and some have zero regulations.