Up to now I aimed to maximize the Repairs and Supplies categories of my Schedule E, to make sure I have as large a deduction as possible.  

It shouldn't take more than five minutes.There's not much you can do to accelerate the process with cleaning and repairs.

@Khayla WilliamsI strongly recommend against borrowing 100% for a propertyThere is significant risk in owning real estate including section 8 and maintaining the home in a certain condition and if you do t have the funds for those repairs you could lose it all.I always recommend people budget and save enough for a down payment and reserves before getting into their first property.

I have heard some say that they save 2 weeks in August for repairs for non-renewals. 

Many houses in Trinidad were built by inexperienced homeowners where you may find lots of hidden repairs.

You will spend 10X on repairs and servicing of a poorly manufactured window so better to spend a little extra up front.I've recently had success using Harvey slimline windows on some rehabs.

The HOA says it only has to fix the leak and is not responsible for the interior repairs.

Manpower, muscle!

Just looked at GNNP home.Would cost too much to repair structural problems(huge crack in ceiling from house settling).

One thing I discovered recently is they make heavy use of the Schedule E from your tax return, so if you clean up your Schedule E (eg by minimizing repairs and maximizing CapEx and accelerated depreciation), you should be in much better shape.