Offered to intern/work for him at half the pay as his personal assistant if he would teach me everything he knew.

I am just planning. 

Speaking with a lender is a good plan, they can help you plan for the future.  

You need a management plan in a market to make it viable.

I plan to negotiate the rent and I want to present my proposal to show how I’ll manage the property responsibly.

I noticed that the previous owner let them pay half the security deposit and the other half later, which is a red flag.

Your dentist has $4,000,000 in his 401k plan.

There’s no real reason to jump into another market unless your goals shift and your current market doesn’t fit anymore—or if the market itself stops producing the results you need.Mastering one market and squeezing every opportunity out of it is a much better play than spreading yourself too thin and getting half-baked results in multiple places.

Well, what is it when have to give away half your cashflow?

I purchased both as a package and for the next six years enjoyed great cash flow as I paid the tax on the house lot annually at about half of what it should have been and neglected to pay anything on the tennis court lot.