I never understood this idea of 'I want an str so I can have a vacation home a few times a year'.

Keep in mind that refinancing comes with its own costs, and it’s important to calculate whether the savings from a lower interest rate will outweigh these expenses.

That being said, there are some amazing professionals that bring a great deal of value and really protect their clients...and save/make them $$$.

Between all of these websites combined you will be able to get a really good idea of what to charge for rent. 

Currently I am looking at "Your In Town Home" , "Vision Realty Management" just based on the google reviews but would love to get some ideas based on anyone else's personal experience.

The combination of these tools will give you a good idea on what you can expect. 

I might be having trouble trying to convey an idea about real estate investing.

***NOT taking off the old shingles, is only saving you around $1K (give or take)... if you're already going through all the hassle of new system, bite the bullet and do it correctly.When you remove the old layers, you can then: do any necessary repairs; possibly install ISO boards (insulation boards) smoothly; install the good membrane (not simple felt!)

I have around 100k in savings that I would like to put towards the purchase of an investment property in Rochester, NY.

They target OOS that have no idea what the 5th ward is really like, but on a map see it's proximity to downtown and think it's up next.Think you should focus on a solid SFH for your family if you have some money you can put down, and worry about investing when you are in a position of strength.