Honestly I think WL is only for people who are already well established with lots of cash flow and a lot of assets.

The towns to the east have a well-established history of short term rentals/tourism.

The established investors seem to stay rather quite.

Establish your buy box and really get to know the territory in the specific area you are looking at and then trust, but VERIFY

If you have enough funds in an IRA the alternative would be to establish a self-directed IRA, and have the IRA buy the property subject to existing financing (if your sister is willing to do that), you personally can't assume the mortgage b/c you are not allowed to provide a personal guarantee for IRA-owned property and have the IRA pay your sister for the equity.

He came back and said that discussing price discounts that he's established with vendors wasn't appropriate.  

If you look OOS establish a team and learn the area before diving into a deal. 

Establishing rapport during property tours can lead to valuable insights and hidden opportunities.

Once you've established your goals, develop a strategic plan to attain them.

Others will reject the idea because you can't produce an income for their office and will likely be a taker, not a maker.My suggestion is to get a job with an established property management company.