My monthly payment including the $240 HOA will be around $1700 which is very comfortable for me.The unit next door that I'm contemplating buying was bought in 2007 for $430,000.

I have also contemplated the fact of 100% deeding the ownership of the home over to the tenant with the agreement in place of new lot rent price, and 5% escalator per year in rent...possible 10 year term on the 5% and after 10 years the escalator would be brought to 3% annually.

While I do understand the risks and benefits to DIY vs turnkey, I'm still contemplating what my approach would be especially during current times.

We experienced having our Helocs frozen overnight, so I will move quickly on getting a cash out refi on our investment property if we keep it and have been contemplating pulling out the cash on our primary HELOCYes, the stock market is volatile but it's liquid and gives us some diversification. 

I am seriously contemplating doing a buy and hold on a single or multi family home while I rent.

I am active duty in the Army therefore my time is limited (I have 5 years left in my contract).. so I was contemplating where I should spend my free time.

I think if you have to contemplate whether the tenants application is eligible, its probably not a good idea to move forward.

Don't spend to long contemplating this question as this is more of a direct response marketing industry and so much about building a house hold name.

To complicate it a bit more, I’ll add that we were also contemplating doing a flip as our first deal, then switched to the house hack idea, and now are going back and forth on which might be better to start.

At that point I'd consider myself financially free and would contemplate retiring from the 9-5 lifestyle.