I ALWAYS start with the end in mind, and after being involved in managing over 425 properties we have found hat the homes and properties that most consistently spit off cash flow and give you true mailbox money are the ones that have fantastic tenants that treat the home like it is theirs - and those tenants are usually in areas that the schools are rated at least a 5+ on Greatschools.org.

You cannot deduct any expenses that are not connected with your rental units, for example, repairs in your private unit.You are not obliged to have a separate business bank account, but if you want to treat your business seriously, I would recommend you to open one, that way it will be easier for you to calculate your results and file taxes in the end of the year.I hope that helps!

If they have no skin in the game other than labor, they will not be there in the event of a loss-Reality is most contractors would just rather have the money and do not have a system in place to wait for the big prize at the endThe best way to handle the contractor relationship is to treat them well, pay on time and be accessible when needed. 

Contractors pay for each sales lead, so they tend to treat them more seriously. 

Should I be concerned about refinancing of the property down the road due to Agricultural zoning, or the fact that its dual Agricultural-Residential zoning it will be treated same as residential?  

Treat it like any month to month agreement.

So, I would need to treat a wholesale transaction the same way I would as if I were purchasing then selling my own home...?

We're seeking a PM that will treat our Tenants with dignity, respect, and professionalism and that will treat our buildings as though they owned them &  lived there themselves....Does such a thing even exist?

It'll more or less be treated as self employment with the lesser of the average of the most recent two tax years over 24 months or YTD earnings over N completed months in the year, with one-off exceptions to the latter for industries known to be seasonal.... those reality TV Alaska fishermen making $100k in 2 months of work can get mortgages, and real estate agents can get mortgages in February even though their YTD is often $0. :)Start getting a detailed list of employer start/end dates together along with all W2s/1099s.

Decide whatever you decide but try to think of tenants as people and treat others as you would they treat you.