Those Annuities don't sound great, 6.4% yield if just you on the policy and only 5.8% if you add your wife to inherit the policy if you die someday (sorry but high likelihood, nothing lasts forever)consider as recc above, find a few good syndicators with several upcoming deals you can identify within 45 days of the sale of your condos (sell all 15 as a package to some investor), then invest as a TIC, tenant in common, with one syndication deal, there won't be any fees, then make sure it's a longer term 10 year at least investment, then keep rolling until death.

It is very common in CRE to bait and switch or have a loan denied and paying $2k+ for an appraisal and a 1% deposit. 

You need representation that has a lot of experience to avoid common issues like early terminations, performance of that location for tenant, etc..Rule #1 is make sure you are happy with market rents for the building (not what current tenant is paying).

Yes - you should be able to find a lender that is "AirBnBRRRR" friendly - most DSCR Lenders will require the full 12 months of STR history but a few that specialize in STR can qualify less than one year, typically with AirDNA projections or some common-sense mixed underwriting approach

Hi Bryan, we have a lot in common.

It is cumbersome though, and confusing when getting beyond common data entries.  

Common fees will include a set-up fee, a leasing fee for each turnover or a lease renewal fee, marking up maintenance, retaining late fees, and more.

A detached quad consisting of four one bed one bath units will cost significantly more than an infill quad consisting of four one bed one bath units etc..Lastly, there are very few zoning districts in Philadelphia that would allow for a 4 unit building to be constructed in Philadelphia on a parcel that is only 1,000 SF and from a practical standpoint the units will be quite small when you consider the need for open area and common halls/stairs.

It is quite common in buying CFDs not to obtain either of those items.

Investing is a supplement and a hedge, but you earn more for all of your investments, but upgrading your salary or wages year over year.Investing for the wrong reasons (or perhaps, investing with unrealistic goals) is a very common problem in RE.