He even went as far as to  properly install a tin roof in order to have that as one less expense in the future.

Wholesaling is considered a gray area judged on intent, long story short Some brokers & lawyers are for it with the proper disclosures and while other brokers are against it no matter what.In any case, I'd suggest you join a local investment group of some type and ask around for agent recommendations or hopefully there's a PA agent here on BP that'll answer this for you.   2.

Some of our acquisitions will be seller financed and we will need to make sure we acquire the property with the proper paperwork.

Coding correctly is crucial since these financials will have to be given to the Tax Accountants to make sure things are expenses and amortized properly.

A landlord may not terminate the lease, but under the Servicemember Civil Relief Act the tenant may terminate the lease with the proper written orders without penalty. 

remove carpet and refinish sub floor, replace countertops, add kitchen appliances, move a wall to make space for a proper staircase, add a parking spot, replace oil tank if it isn't already a deal killer.Exit: hold as rental long term, sell on a lease optionAny thoughts would be much appreciated.Thanks

I have attended some other places courses on investment and want to look at all angles to ensure I am very well rounded.

Some details of  contracts to ensure that you and your tenants needs are more sufficiently met with snow removal.  

Again, we'll ask for 30 days to do walk throughs of each property, meet the tenants, determine the status of each rental, verify current market values and ensure that its a great deal from that perspective.

I cannot say if you should move your rental to a legal entity or not, but I can say that a legal entity if properly administrated can offer you additional personal liability protections.