I am also an appraiser that works with local and out of state investors make connections with local investor friendly lenders and property managers.

My life situation:I live and work in Aspen, CO from December - April.

I’ve spoken to a few, but they didn’t seem motivated to work with me or would say one thing and do another.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

We are currently looking at three types: contract for deed, seller finance, subject to.The hurdle is, we both have no experience with special types of financing and have no idea who to talk to.

.#2 Set a schedule....lets say you work 8-5pm FT job....then you work 6-10pm calling, prospecting 5 days a week and 8hrs on Saturday and 4hrs on Sunday afternoon.#3 That's 32 hours a week for the first 6 months after your FT job. 

Hey Sean, if you decide to invest locally I'd love to opportunity to work with you if your properties need any work done.

It actually pisses me off that he decided to go this route instead of just calling me to work something out.

My question is, when is it the right time to start using a property management software and which one would work best for my current situation.

No, you said how does one find a "deal" without a wholesaler, it's very simple, you simply put in the work to either (A) be found by these sellers who are "deals"     -OR- (B) you approach them yourself.