Depending on your reinvestment opportunities (return rate) and your opportunity/hurdle costs of other capital sources, an extra $2700 in pocket today, might be worth paying an additional 50K for the asset.One might also convince themselves it is a better choice to pay 2.5 times more in the way of interest (252K) in exchange for $1100/yr in pocket and the security of a fixed payment for half a century ... though, personally, the inflexibility of being corralled that long could never be worth it.  

Have your tenant check with a lender to see if they qualify for a mortgage and have a sufficient down payment to buy the property from you.Not sure why you would sell to them and keep their payments low unless you are just trying to mostly get off the hook from paying the HOA dues, insurance and property taxes. 

Good choice, I think.I guess I'm going through some kind of mid life crises.  

You have several choices.  

Your choice, BUT a 10yr roof is not 'in poor condition' unless A) it  was installed 11yrs ago B) an inspector says so in writing. 

Success is a process, failure is a choice

However, If I did not have sufficient funds for 6 months of debt (PITI) service, I believe I would be over leveraged.

As I learn more about rental properties, flipping houses, property developers etc, I feel over whelmed with the knowledge and the choice of roles played by REI broker, licensed agent, developer etcThe ultimate goal is to develop properties (commercial and corporate).

As I am reading around I am wondering if this strategy occurs or is even possible.  In buying a home for myself if I notice a house that has been for sale for a while or is for sale maybe through craigslist is it poss...

Andy, Solo 401k plan is not for everyone (you must be self-employed or own a small business without full-time employees other than the business owner(s) and spouse), however if you qualify for it - in most cases it would be a much better choice for most people (you don't need a custodian with it, you don't need an LLC to gain the checkbook control, you can borrow from your plan up to $50K before retire, just to name a few advantages).