I have cash on hand and plenty of free time for now so that’s a benefit but I’m afraid to make any moves with out working confidently with a seasoned investor.

I would just like some advice/recommendations in this area to give me more confidence as this is what I would be worried about most (obtaining the financing and exit strategies if things don't go as planned.)I apologize for the long post but I'm excited about REI and find it hard to contain that excitement in a community such as this!

After all, it's your hard earned money that you're investing, thus you should do what you need to feel confident in the investment you are allocating into. 

I wouldn't worry too much about the time of year - prolific flippers don't stop just because the season changed.The experience you get here could make you much more confident on future deals as well, because you'd be better at every part of it.

I know I should have exit strategies just in case they don't, but what steps can I take to be confident they will refinance?

(I do own another property of similar size close to this property so am fairly confident in my assumptions.)

I now feel very confident that it's time to move onto slightly larger multi-family properties. 

I also don't plan to buy in this area in the near future unless it was the only deal I could find that made sense in a 60 mile radius assuming I can find good tenants for the first deal and I was confident that I could keep duplicating those results.

The contractor was confident things will go smoothly when he gets in there and starts the process of working with the insurance company although as a back-up plan I could hire a 3rd party adjuster as some mentioned above. 

I have heard some different strategies over the years, but the DST is the only one I have ever been able to confidently get behind with all the legal implications.