I would not buy a rental with a pool unless you were in Vegas PHX  those type of areas.and I would pay for a pool service your self if you do buy one with a pool.. they are liabilities both functionally and a accident waiting to happen.. someone drunk diving into the shallow end and getting hurt... kid falling in and getting hurt etc.you won't get any more rent for themGhetto   NUFF said about that..

:https://www.biggerpockets.com/forums/52/topics/680...Without providing a laundry list, I think the theme is to tackle the wear points and troubleshoot the individual unit.For example, start at the door (door mat to catch debris, good functioning new lock, perfect close and open, door stop) and work through each room with that level of detail ( example: Bathroom: new shower curtain, bath mat, caulk, new toilet flapper or overhaul kit inside, strong towel bars, etc.)I would focus first on the low cost items that can prevent larger problems (your doorstop type theme) and then also evaluate any larger item close to the end of its useful life, especially if showing signs of problems (be it hot water heater, worn flooring, or an appliance). 

I called WE and learned that the average cost of utilities combined is $397/mo.

I forgot to mention, you can combine the Purchase & Renovate with the Energy Efficient Mortgage (EEM) to add even more to your rehab budget (like Windows).

I've looked at the value and it's over $3 Million combined.

The actual numbers came below:Purchase: $98,752.00Renovations/Holding: $79,211.54*Sold Price: $207,500.00After Closing Costs Profit was $24,066.10... with the caveat that it was a combined effort with my father and the split was $12,033.05.Long story short, the house was purchased in Nov 2015, worked on between 3 other houses I had/have, and sold in March 2017.

Is that bad luck or a function of the market/soil?

If this is a low end rental I'd make sure everything is clean and functional and use as-is.If you are looking for something a little better maybe leave the cabinets in place but install new laminate counter tops, sink, faucet, and mid-grade appliances.

You allocate that based on square footage, so if all three units are the same size each gets one third of the cost basis, but if the main house is the size of the other two units combined then it'd be half to the main house and a quarter to each smaller unit.

I have always believed that timing was more a function of my personal situation than the market.