You'll need to be prepared for heavy vacancy, tenant turnover, R&M, and CapEx.

It COULD make more sense for you to outsource if were going to scale up to 50 doors AND found the bookkeeping too time consuming.Its what works for you.I did all my own management, bookkeeping, tax return preparation, pay bills, etc. for my rentals and still worked my day job. 

Getting a tax preparer to take an aggressive position on a return is not the same thing as what the ultimate correct position will be if you are audited (plus interest and penalties).

I believe the best thing you can do if this situation occurs to you and your appraisal comes in lower than expected is to be prepared with valid comps of your own to make the case against the lower valuation.

Sub-to laws vary from state to state, so definitely make sure any legal documents were prepared/reviewed by a local lawyer familiar with this transaction type.As far as whether someone was taken advantage of...

All you would need to say really is that you materially participated in the business during the tax year and just be prepared in the case of an audit/IRS notice.

Prepare any documentation that can support your income stability and creditworthiness.

I would also recommend looking for a tax strategist who is willing to work with you throughout the year, not just when preparing your tax return.

For anyone whose interested, here's a link to a recent paper that compares one flavor of AOL to traditional title insurance, prepared for the MBA. 

If property values don't appreciate as expected or if circumstances change, you should be prepared to pivot your investment strategy.The strategy proposed by your lender has potential benefits, especially if you're confident in the appreciation potential of the market.