In essence, I'm pay up front and then reimbursing myself once completed. 

Of course as an Owner you too can seek out and attend the seminars and classes noted above, however the HOA is not typically authorized to reimburse you as a Non-Board Member.

If the water bill is not paid by the due date, landlord will pay the balance, add a $25 service fee to be paid by tenants, and then give tenants seven days to reimburse landlord for the water bill."

Unless otherwise specifically stated or provided, Universal Property Management will obtain and pay for all required building permits and Owner will pay assessments and charges required by public bodies and utilities for financing or repairing the cost of sewers, storm drains, water service, and other utilities including charges for sewer and storm drain reimbursement, revolving funds, hookup, and other similar charges. 

It was a bit of a gamble up front because I paid for it myself entirely while pretty much all of my classmates had tuition reimbursement through their employers (for instance, a few of my classmates worked for Disney,  who pay their full-time employees 75% of their education costs.

Probably have all agreements in a contract that if any tenant have done that, you can get financial cost incurred in repairs be reimbursed to you.Just charge it to experience and move on. 

But if you do a 1031 it's a different story - You say it's reimbursement of expenses - they say it's profit when you do a 1031 and take cash out.

Many in the medical field though are frustrated with pay systems and healthcare reimbursements.. its not all wine and roses :)  but the folks I know in medicine like you say do quite well and are intelligent enough to invest wisely. 

There are water systems that are private that can be put in place in some cases but even then not all tenants reimburse on time for utility or at all.

At the end of the year, I would submit for tuition reimbursement from my company...since I had already taken out loans to pay for tuition, I decided to put the reimbursement chunk toward my down payment savings and get across the finish line.