A personal home is a life style choice not an investment and will cost you far more to own than renting will ever cost.

Yet, they have different styles such as a front porch or an archway.

A building the same style on the cul de sac I'm on sold for $153,000 farewells ago.

'Positive Mental Attitude' Hawaiian style. 

I have a back door of a rental unit that has a large glass section (as seen below); and I wonder if I am potentially liable on either side if...1) Someone just breaks the glass, reaches in, easily unlocks the deadbolt...

A freelancer that works for us sometimes is a 'digital nomad', though she is a bit younger and I think she does it more with shoe-string style finances than you're looking to do ;) While I, of course, always recommend that people invest their money to make it work for them and provide stability, I must say her life sounds pretty neat.

Because of this I am considering other styles of deals beyond the simple cash deal, such as owner financing.My struggle is that I am not sure how to calculate the repair costs.

A personal home is a life style choice not a investment. 

Off-white shaker style known as being timeless, as the chances are good I won't be updating this kitchen again in my lifetime. 

Might be harder to buy though, because you are competing against retail buyers.I don't think they are that different, more a matter of style.