If you go the route of self-manage, do it ahead of time and YOU synch the rental company calendar with your calendar.

All things being equal as holding will eventually need repairs on homes etc.

If the home is outdated and needing repairs, could a lease option strategy work? 

If not, you might have to negotiate the repairs will need to be done prior to closing.

It will help you track things more clearly and you'll be ahead of the ball come tax time. 

I am really not too sure that I calculated closing costs or repair costs accurately.

The only negative I can think of is that the current Owner possibly may be deferring maintenance expenses or any repairs or replacements to make his/hers expenses look better along with the bottom line. 

The repairs were estimated at $250k, which included completely redoing everything and building the addition.

As long as the cost of "putting it to work" is less than the return on that work, you are ahead...and your equity/cash/money is no longer dead.Money is not a noun...it's a verb...or it should be in order to win.

Make your current properties better such that you will have less repairs later or you can defer repairs when times are not good.4) Self manage your properties if you can.