However, there are lot more experienced investors at that meetup compared to a lot of the OC meetups I have gone to.

It might be unnecessary, but something you should look into prior to selling.Your plan isn't crazy; it isn't something I would want to do because I wouldn't want to move every 3 months but if that suits your personality then it could work. 

I currently have 100K in the bank doing absolutely nothing and I want to get the best bang for my buck in terms of properties/investment.I figured that if I am able to invest 100K outside my state, I would be able to buy several properties and put them to work for me compared to just buying one here in NY. 

I financed the best one conventionally at the highest appraised price possible, then had them carry the others at a comparable discount using some of the loan money as DPs on the seller financed properties.  

Unless you purchase at least 95% of the value of your list.My recommendation is always to get the new property under contract during the 45 days after the sale or in the short period before the sale happens (you can go into contract for your replacement property prior to sale. 

I do not think this was a major strategy killer, but the house sat empty during peak rental time (Summer before school started) and is still vacant at a price above Proforma.Some Observations: Closing costs came out to be much higher than the proforma estimateTaxes were spot onProperty Mgmt. fee spot onThe vacancy is listed at 4%, even though PM says I takes an average of 45 days to rent, so it’s a broad average I’m assuming after tenant leases or across all their properties.They advertise 2-year leases during the tour and most turnkeys are rented prior to closing, not the case for my property, still vacantOne inquiry has come in for a family whose house burned down, but they want 3-month lease smack in the middle of winter for another renewal, not optimalNeither the marketing department nor PM inside Reedy was very proactive as far as communication.

I'm a numbers person, so my strategy would be to create multiple scenarios and compare them side by side, looking at how long and how much it will take to move you closer to your goal.

To quickly evaluate a a deal where there is no asking price, I usually look at capex required, adjust the property taxes (based on comparable sales) and perhaps play around with the vacancy and reserves.Is there anything I am missing?

The BP calculators are a great resource as well as looking at comparable rents in your area.

(The prior lease was from the previous owner).