You need to know their debt, terms of debt, motivation, and where the debt is on each property.

What's the motivation for the experienced investor to JV?

Motivation! 

It wold depend on how motivated they were to sell.

You can win with either strategy (Buy near market and let it appreciate while the tenant pays down the principal and you get the tax advantages, or BRRRR somewhere with easier inventory selection), but in a seller's market to get a property and the discount you want it for you're basically going to have to steal it from somebody.In that case, you're going to need a motivated seller.

Although if you really want to be an agent full time, joining a successful motivated team is probably the best thing you can do - meet with several different teams with a few different brokers to see who you feel most comfortable with.

Obviously, I need to improve my lead generation to find more motivated sellers but the subject of price lead to do some reading on different financing options.

I would definitely start with listening to the bigger pockets podcast, very good source of information, ideas, and motivation :)

Is $2000 enough money to keep him motivated if the job goes over schedule/budget?

Too much competition.Get a list from the city or county of housing court violations and youwill find highly motivated owners.