I did some repairs and I hired a few tradesmen (handyman, electrician, plumber, etc.) to fix the place up as it needed some repairs/upgrades because the two prior property managers did not take care of the place and the owner was living out of state. 

I looked into upgrading to buildium and/or appfolio but couldn't justify the added cost for where I am at.

Your more budget conscious shoppers will know that they can go a mile down the road and get a SFH in Sherwood Forest for +/- $500k. 

Currently no mortgage on either (I own them free and clear) and both in great shape (we were fortunate to be the beneficiaries to substantial grants that allowed for new roofs, furnaces, upgrades, etc, in 2017).

Taking that first step though...Daunting.Finding the deal, picking the right financing, finding the right contractor, picking the most economical upgrades for flip that still yield good rental incomes, and so much more. 

Also, you want to be conscious of your agent's time.

If they are HER friends, you probably don't want them anyways.Time to give yourself an upgrade to a NEW and BETTER resident.

Like paying property tax yearly, repairs, or even upgrades(say forced appreciation of 3 to 4 bedrooms).Is there a custodian account I control?

Purpose of financing: purchase, rate/term refinance, cash out refinance, upgrades/reno, construction, other (specify).Purpose of financing is to be able to purchase a property.

Are there other, more minor repairs/upgrades you are planning to do for her unit at some point?