Rates are super low right now, lenders aren't being as tight with qualifying credit scores, rents are high, it all adds up to homes being able to sell.  

It went on for pages of crabbed, tight handwriting. 

Both areas are tight markets at the moment.

Either you take your chips off the table, you hold, or you keep buying chips.Bruce says affordability at 30% should have room to go lower, toward the 17% of past cycles; BUT ON THE OTHER HAND, lending is so tight that things could be different this time.Harry Dent has strong opinions about the near term future of the market; John Burns has equally strong contrary opinions.  

A lot of great info and ideas directly related to your OP question there, regarding the project manager question, I'll focus on some important issues involved because it is in Shorewood and these are truly important issues.I lived right over the Shorewood/City of Milwaukee border on the east side of MKE for years and know a fair amount of people who have and now live in their own homes there, a few people who've owned rentals or lived in half of a duplex and ONE person who rehabbed and flipped there and made some profit, not sure how much.Shorewood, more than ANY other suburb in the entire metro area, is from what I've heard over 10+ years of doing this and other RE investing related stuff, TIGHT about what goes on with any property in the village and NOT a place where you want to be employing any contractor who's going to be cutting any corners or anything like that.

It's called being a tight-wad on your housing expense!

With all the HOA fees, mortgage that includes taxes and interest along with vacancy and repairs, sounds too tight.  

Our concern is that getting the loan will be tight, it was last time, as we have 2 mortgages already and high monthly living expenses (NYC) and we are both self employed.

I have noticed that nearly everyone is generous with 'general' information:Use FHA financing, invest for cash flow, build connections, etc.However, many people are very tight lipped with specific information:Who is your broker in {metro area here}, who is the best property manager in {metro area here}, tell me your favorite zip codes, etc. 

This increase in the hydro bill is going to be due to either increased consumption (more kWh when compared to the same period last year) or a rate increase on the part of the utility (this would include tired pricing).If increased consumption you have basically three causes:a) Tenants keep the place warmer and/or consume more hot water than last years tenants;b) The weather in the last billing period has been colder this year than the same period last year;c) Your building envelope is less airtight than it was last year or one, or more, of your electric resistance heaters have failed (the thermostat issue raised earlier).Even though you have made no changes to the property, there is the possibility that something as simple as a piece of weatherstripping on/in a door or window has failed (or maybe window is not closed tightly) which is causing more air leakage.As mentioned earlier, a thermo camera will help you locate air leakages and heat loss through the envelope, but you still will not know which of the leaks is new and which were there last year.