Until that point you will be paying out the @$$ for insurance, with your standard policy + specialty vacation rental insurance.

Once I find the right tenant, do I just sign a standard lease agreement with them?  

He is quoting $3000 in labor and materials for replacing 10 windows (including one small window over the sink in the kitchen) with standard vinyl replacement windows. 

I have heard of people renovating basements so they can make it into a rental.Make sure when renovating a basement that it can meet Massachusetts Building Code and the Minimum standards of fitness for Human Habitation otherwise the tenant can take advantage and not pay rent. 

As an aspiring multifamily investor, i would like to hear from others about what has worked for them as far as raising capital for deals...Apart from hitting up family friends and co-workers...I was wondering if anyone out there has any out of the box ideas for finding investors and raising capital....Is there someone out there that has had some success with a method that is not maybe the standard approach?

Here's an example of a current place available in my area:140k asking price$1,485/mo in rentLooks to be a solid place, needs a little cleaning but otherwise it's pretty standard.

Sorry for the long intro, on to the topic.We are going to look for a property to purchase in our expensive market by my standards (300 K-400 K) for a decent place in good school districts of South Tampa in the next year.

Additionally, if anyone is able to share any kind of Standard Operating Procedures that may model something like this, that would be greatly appreciated!

You will need to look at what is selling in that area and conform to those standards.

You can qualify either by meeting a set of standard requirements (the “safe harbor” provisions) or by showing enough facts and circumstances to validate your claim.