Difficult to make decisions, and can become gridlocked. 2.

Any tips or past experiences on either options would be gladly accepted to help make my decision on which route to go with.

These weren't all-encompassing features but enough for me to make a decision.

You should also consider whether you want to sell the improved lot or rent it out as that will have a huge impact on your decision.

They handle all of the legwork, you make the final decision, and you essentially exchange time for x value, which depends on the firm and the individual deal.

If I make the decision to sell this property and take those profits and buy several land contracts (homes for sale by the owner through land contract agreements) will I be able do a 1031 exchange?

Could be the fear of going into a large investment alone that stops people from making a decision.

First of all, I would make the decision from a zero basis. 

I will ask my mortgage broker if the vacany made a difference in the final decision but I believe the decision was made assuming the grandfather status was still in place.

So my decision basically comes down to easing into being a landlord and rent my current home (est. $300-$400 cashflow) or leverage my current equity to try and get something that cashflows more and jump right into the deep end (assuming I can find a deal that would cash flow higher).