This could be easier certain parts of the year as well (like winter for example).These also have some good feedback on your approach and how others evaluate:https://www.biggerpockets.com/forums/12/topics/150...https://www.biggerpockets.com/forums/52/topics/175...

The property does not have a yard so the only outdoor expense would be plowing the parking spots in winter.

I was hoping to purchase my first multi-family before winter but I feel like I need to reconsider that goal as that is less than 3 months away- I'm not ready!

Happy holidays as well. 

The damages are time planned off-work for fix the property for an October 1 rental date, cancelled contractors, but most of all missing an October 1 rental date which puts us in risk of having extended vacancy through a New England winter. 

Park Paid Utilities (overhead lights, empty trailers that need heat in the                                               winter,etc)               -  $150?  

Our plan, like many others, is to begin in contract assignment from North Pasco to South Pinellas, then sooner than later snag a few fix-and-flips and ultimately buy-and-holds in the Holiday/Tarpon Springs/Palm Harbor/Clearwater area.David and I each have 15+ years of applied background in marketing, sales, interior design, and are both now on track to obtain our RE License.

I know it's easy to find seasonal tenant for the winter month but I intend to rent it all year around.  

I'm curious as to what to expect for vacancy during the peak months (May-Oct) and I can only assume best case scenario would be to find short-term tenants for the duration of the cold winter months.

I agree about number not being the best here, i would be afraid to be to far for my investment, rural areas have a low quite market and if you go as far as another city probably will have to get a property management company.My ideal price is around 350k and can go up all the way to 450k, timeline not really sure, probably wait for the winter, January or something, prices go down, people want to sell, if vacant is hard to rent, so sell could be an option for many.Plan right now is learn a lot, look at the market, mls i guess and specially property's that are there for a while, then when the time comes, make an offer that makes you feel a shame.I recommend also to look at open houses whenever you can, i go all weekends, that has help a lot, is helpful when you want to have an idea of a house price.If there any property that you want to consider, private message me, id love to have a look and help you come out with the offer price, as what i'm focusing now is Estimating and pricing.