They passed new loan regulations where I only need to put 3% down on owner occupied 2-4 units, which is where I plan to start.I do have skills.  

Unless you can find somebody that isn’t concerned about all the regulations surrounding consumer loans … not suggested.

Pricing is typically based on loan volume.These solutions will help with automating tasks related to complying with your state's regulations around private lending.

Please be gentle; I'm new at this and it's pretty complex :)Structure / Legal Details- we'd establish market value through a combination of comps from local real estate agent and an appraisal- attorney would establish all required "arms length" aspects including a mortgage at a minimum standard federal rate- LLC would pay us back based on a standard promissory note over 30 yrs Pros of selling to the LLC (I think)- A sale now would be the only time we'd be able to take advantage of the cap gains exclusion on this house bc we won't qualify for the "live there 3 of 5 years" rule due to the timing of our lease and our last time of residence. 

Roseville and Rocklin are great areas for long-term stability and growth, but the prices are quite high and the rents are LOW, and they're not friendly in terms of regulations for STR. 

None of the names listed above appear to be pivoting into the homeowner association space, yet here in the northeast USA it's still quite a fragmented industry outside of the major urban centers with established and deep-pocketed PM firms. 

Furthermore, what are the regulations regarding security deposit?

Additionally, I appreciate the note on Madison's strict short-term rental regulations for non-owner-occupied properties.

If it was built before, say, 1960 there may be a slew of electrical work you'll need to do to stay in regulations with current times and, of course, for the safety of a future buyer.

City regulations aren’t allowing for any more str licenses, but we could still rent it out as a 30-day rental without needing a license.