Hello,I am hoping to get advice on whether or not I should switch my home from a typical annual rental agreement to a vacation rental. 

Personally I wouldn't upgrade from 08 to current if I had to pay unless there's some new feature you really need.

Couple of things, you may not be able to convert the garage into a studio apartment, that depends on your zoning, and that goes for @Judy P. idea about splitting the property into two lots, it all depends on zoning and what you are allowed to put there, but if the typical lot is an acre or less, i think she has a good idea, i wouldn't sell just yet until you did some research. what town do you have the property in ?

So essentially I would like to funnel all of my cash + future cash towards building a rental portfolio and flipping homes during the downtime at work (storm season starts around march and typically ends by November).What do you guys think?

Its just more paperwork during a renovation than one would typically do.  

Do you guys typically go to attorneys to have them draft up the lease?    

FYI - The quotes do include wind (hurricane) coverage which is a necessity around here.Are these quotes typical?

We have vacation rentals with lock-off feature in a few of our complexes here.Let me know if you would like a couple of examples.Aloha,Jeff

I typically subtract 3%, of the ARV.Realtor Fees: What is the commission you are willing to pay your listing agent (unless you are the listing agent) and the buyer's agent.

QuickBooks Pro has a feature called "Class".