It sounds like you are on your way towards that which is great.

Don't decide on wholesaling now because most likely that will not work out for you.

I can get you a free guestpass if you like. 

I would like to stay in an area I'm familiar with until I get comfortable with the entire process.

I would greatly appreciate any tips your friend would like to share. 

To "soften" or reach a compromised we agreed to ONLY have $30K of the $60K in funds be considered "OPTION CONSIDERATION" funds (giving us the EXCLUSIVE RIGHT to buy the property at the $300K Purchase price) and the OTHER $30K of funds would be STILL be given to them but we informed them that it likely will be consider TAXABLE INCOME to them.

I am assuming 10% vacancy, 10% repairs.A couple things just came up during inspection and I will likely try to get a lower price but I don't think I will be able to get it.Should I just go for it anyways? 

Would a property like this be better suited for long-term or short-term rentals in your experience?

As noted above you can likely keep the bookings for a cost. 

I’m here to learn and start my REI journey while hopefully meeting some like minded people along the way.