I'm not super experienced, but I did go for my real estate license a couple of years ago.  

I'm looking to fix up my single family home and then sell it to move to another area.

Maybe buying a single family and renting rooms would be a better option for you.

It's going to cost you a lot more to replace a roof on a single-family home then what your condo association would charge you to put on a new roof.

Both companies have market rates - but their pricing is not super retail/premium.

Ross Ellington , if the sum of your mortgage interest, any points, and property taxes exceed $6,300 for single filer or $12,600 married filing joint or $9,300 for head of household THEN you would elect to itemize your deductions and lower your taxable income by the sum of interest, points and tax.

Currently own 3 rentals in South Boston (2 single Families and 1 Condo) and also own a two family in the Adams Corner Area of Dorchester. 

Cash flow can be inconsistent for one single residential property.  

Michael,I am planning to buy/hold.I only own one property my primary residence which is just a single family home.The value of my primary residence is 80k.Thanks for the response!

My crystal ball sees you in a single family home in a nice town in Westchester somewhere.