It's actually quite interesting that typically the folks with the most transactions under their belt are the folks that you as a consumer have the least contact with, and the least experienced folks are the ones you have the most contact with.

This is just a theoretical that popped into my head, but for those markets where rents are relatively low, would it be reasonable to take on a tenant with the typical one month's security deposit, but in addition you add $50 or $100/month to the rent to build up the deposit till it hits two month's worth?

Most people don't know that your typical insurance agent from a big name company has very little experience in working with investors, especially investors that are also contractors or GC's.

Solar typically takes 15+ years just to break even so how are they producing enough income to pay you for renting the roof?

We aren’t trying to earn a ton off of this, hoping to just do a couple nights a month for an extra $1,000-1500 a year that I can put towards our investments.

Talk to your attorneyFor answer #2 & 3, you would typically use what is called a KP (key principal) and that person would help you qualify for the loan. 

Private or Hard lenders such as us would not typically finance this deal as we do not / cannot lend on owner occupied properties. 

I know some people disagree with me, but this is why I typically do not secure a new tenant or start showing a property until it is vacant.

Your numbers are above that; so, your audience will be the typical high net worth individual who invests in passive real estate. 

We typically have the most success in those areas.Hope that helps,Chris Pre