(I super simplified this not taking into account reduced interest from accelerated pay down)Example 1:Mortgage 150k (paid down additional 50k) and 50k needed for next downpayment.Monthly mortgage payment $1000 (not including taxes insurance etc)Cash left after 2nd purchase $0Example 2:Mortgage 200k, 50K needed for downpayment, 50k in reservesMonthly mortgage payment $1000 (not including taxes insurance etc)Cash left after 2nd purchase $50kWhich example looks safer?

I don't know how to simplify the transaction with the seller, I guess the only thing you can do is to say that you are a buyer and actually buy the property. 

I have simplified it, but you get the idea.  

These are my current income streams however for many reasons I feel like they could be simplified and/or made legitimate.My 'income' from the managing of rental properties however because there is no company it's really a 'gift' from the trust so in the eyes of lenders it is not actually viewed as income (nor is it really enough to qualify for a loan). 

From my limited reading it simplifies things at tax time and offer a layer of asset protection.

I love how people try to simplify it to "what goes up must come down".

Perhaps I am over simplifying?

If it's hard to evict a tenant, then a month-to-month simplifies things because you can get rid of a bad tenant by issuing a 30-day notice (assuming they honor it and leave).

The better the returns, the faster you reach your goals.As for strategy on your goal.. let's simplify and say your goal is $5k/month in cashflow. 

Simplified to clear the concept.