I would talk to agencies on south shore too, your pruce points in Incline are much higher than south shore or other points around the lake, I dont know that your rssoective rental rate and  booking density would justify it.

@Tim LaBelle You are correct, we are not quite as agressive as most of the costal cities, but like Rebecca said the North Shore is one of the most desirable neighborhoods in Milwaukee, properties in good condition go fairly fast, typically in days and we have seen some solid appreciation in the last years.

I've been watching out for possible Jersey Shore vacation rental deals for a while now and might have found one for which the numbers work.  

Keywords: loop / Woodlawn / Bronzeville / deering / south shore / Chatham / Washington heights / calumet heights / south side Chicago 

However these are temporary loans (1 year or less) and you will have to refinance after renovations.

http://www.har.com/content/newsroom/Houston Real Estate Highlights in October Single-family home sales continued their post-Hurricane Harvey rebound as volume rose 7.5 percent year-over-year with 6,381 units sold;Single-family home sales remain 2.8 percent ahead of 2016’s year-to-date volume;Total property sales increased 6.6 percent with 7,614 units sold;Total dollar jumped 10.8 percent to $2.1 billion;The single-family home median price rose 3.9 percent to $226,491, which represents an October high;The single-family home average price increased 2.7 percent to $285,858, also the highest level for an October;Single-family homes months of inventory grew year-over-year to a 3.9-months supply, but is down from a 4.3-months pre-Harvey peak – the result of a surge in consumer demand for housing;Townhome/condominium sales rose 5.8 percent, with the average price down 1.1 percent to $195,393 and the median price down 3.1 percent to $153,000;Leases of single-family homes rose 13.6 percent with the average rent up 2.8 percent to $1,776;Volume of townhome/condominium leases jumped 34.8 percent with average rent up 2.9 percent to $1,533.HAR still encourages anyone who has housing available for temporary occupancy (up to 12 weeks) to please post it on our Harvey Temporary Housing page at www.har.com/temporaryhousing to provide housing to those in need.

However he needs to shore up, rebuild trust and act with integrity.

Most all of the structures are fairly temporary in nature of construction, so down the road, re-purposing the land would be incredibly easy. 

The basement under this large room was full of water and had a bunch of temporary support posts pushing the floor joists up (physically bowed up).

My wife and I are willing to self manage(buy ourselves a job), but the numbers still don't make sense on the south shore, and self managing any other side gets difficult.