Should the holding company be an S corp or LLC??

I talked to asset protection companies, Prime Corporate Services and Anderson Business Advisors (both have mixed reviews).

Those that respond “$0” or something ridiculous, you can request income documentation from them to justify.Don’t be afraid to share with them how much your property taxes & Insurance increased and that YOU cannot afford to absorb them.ALWAYS get an increase or something of value annually or tenants will start thinking they should never have an increase, making future increases that much more difficult to negotiate.

Most lenders but not all, should use the existing 2nd unit lease at 75% of gross for extra income to qualify on either loan types.

If you don't have patience or expertise or time I would just sell and 1031 exchange into a property that generates income, appreciates and helps build wealth.

If you're looking for basic income/expense tracking, I'd suggest checking out Stessa.

I am not sure how long each property needs a rental history in order for it to be counted as income, if they only count a certain percentage of this income, etc. 

I made more on two flips in a year than at my Full Time CORPORATE Job.

Really and how will he do this with zero income, and only 50k ? 

That would eliminate my current ~$1100 monthly cost of living renting and pay for the house itself with rental income