I’m located in the suburbs about 30 miles outside of Chicago.

There are a lot of homes that need a lot of work so it would be done within a year to a year and a half, new paint, new appliances, cabinets, flooring, etc.So what y’all are saying is I would need to make the LTV go up by 20-30% to be worth it?

While the rest of eastern MA might get a cold rain, that part of the state gets snow - and a lot of it.I didn't see a landscaping budget item, but you'll need one unless you're doing it yourself.Area rents:There were ten 3 bed rentals that were rented within 1/2 mile and within the last 6 months.Low was $900, high was $1,300. 

The idea is that I am looking into purchasing a vacation rental property within 100 or so miles of where I am located and want to know the areas to start looking.

Half the time you don't hear back from these folks for days only for them to tell you they "sold" the property before you emailed but they can add you to their list for the next one.  

I'm out of town the back half of this week so I'll reach out next week to grab some coffee!

Most people are paid twice a month, so you get half the rent on each pay day.

We are in a situation where two tenants (1 male and 1 female - friends but, not a couple) leased half of a double a few months ago.

WE have the GC's lead come in last half hour to get any major issue directly addressed i mean its their responsibility to fix any thing and many times inspector and GC clash inspector says not to code but inspector is not right..

They could be testing you to see what they can get away with.It's the 17th do if they paid the old owner for April, you should have gotten a partial payment (if it was part of your contract) for a half month's rent as part of the closing.