House hacking in a 4-bedroom here could absolutely work if you run your numbers carefully and stick to those “higher-end lower-end” neighborhoods.

We help our clients:1) Find a fixer-upper to buy2) We get bids3) Negotiate a Scope Of Work with the owner using "Maintain to the Neighborhood" to avoid over-improving, but understanding we will have to pass city Rental Inspection to avoid being a slumlord.4) Provide multiple jobsite videos to show progress and document WHAT was done and the QUALITY.5) Handle passing city Rental Inspection6) Find a tenant with a Replacement Guarantee per Class7) Assist with refinance, so client can repeatSo, why you looking OOS again?

Given this is first investment, I would like to keep it local.Any suggestions on neighborhood with good rental cash flow in Middlesex county ?

I'm in the midst of renovating a property in a high end neighborhood.

Regardless I'd think if you reached out to boutique builders, brokers, commercial specific architects, there'd likely be a beneficial relationship there and some organic mentoring that happens.  

I do like the efficiency of pricelabs in terms of easily monitoring your comps (if you use the Neighborhood tab and load in your comps)

I generally rule out most single family homes as viable rentals, as prices are pretty high relative to rents, so aside from some downtown neighborhoods, typically you do not find large areas of single family rental neighborhoods (a median sale price on a 3 bed, 2 bath home so far this year in Dane County on MLS sales data is at $430k). 

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.

This is especially true for the city and for most of the trendy neighborhoods.

The guest rules state no partying and it is abundantly clear our houses are in neighborhoods with full time residents they will be caught and they will be removed without refund.