It must not be too much of a premium beyond basic coverage though considering we got a good policy with decent deductibles  on the beach house,  2100 square foot 4 bedroom only $3100/year --- even with the short term rental liability on it.One more thing. 

Hi All,What is the average/typical rehab cost per square foot in Winter Garden?

Any tips or something you would recommend a begginer to get that first foot through the door and get started ?

Just simply a personal opinion.Oftentimes looking only at price per square foot can be deceiving when comparing homes with the same number of bedrooms. 

If this were a flip property, it is likely an additional amount of SF would result in a higher sold price per square foot (PPSF), however there is no guarantee.

I currently live in a very high end, 1910, 7000 square foot house and I'll guarantee we are running some knob and tube -- no worries on insurance, and anything we gutted and redid we rewired, but the rest we left alone.

We are wanting to do a long term rental on a single family home with a dock for a 50 foot boat that we can use when not out cruising and can do a short term rental 5-6 months out of the year while we are away.

I think it is more my conscious deciding what is right/wrong rather than logical thinking.With them being new tenant to me, I know I don’t want to start off in a bad foot where they resent me and miss appropriately treat the property out of spite.

Brexit, China, etc. we're getting closer to the end of this bull run and I'd rather be positioned well now versus being on the back foot when it comes. 

When you purchase I would recommend having a mobile home inspection completed to make sure that all the tie downs, and footings have been done properly.