I am looking for anyone who has done this successfully and has any advice for someone looking to do some of the work himself and eventually split the utilities to convert into a top and bottom duplex. 

Eventually you plateau because of this.I want to be in a situation where scalability is not an issue.

I know that you can elect to expense certain items rather than do depreciation, there is accelerated depreciation, which they will start phasing out next year, but gross income and expenses will eventually show a profit if you keep operating it well. 

I’m just trying to plan ahead for the eventual need I’ll have for a handyman.

Second, if you are thinking a new build, this entails things like a construction loan that eventually becomes a full standard mortgage.

I eventually see myself flipping houses and doing buy and holds, but right now I do not have the capital to do so.

Ideally, you'd build up savings to eventually cover 6 months to a year of your annual budget.   

That's a new consideration for me to know others may not be able to easily finance when I eventually sell.I don't see how that makes any logical sense from a lender (or note holder) risk POV - if the current structure could be permitted and rebuilt to it's current use in the event of destruction, why would the lender care?

We came in at $825K, eventually settling at $831K.

It seems pretty common place to just lock in the fixed interest rate with the expectation of eventually refinancing to a lower rate.