I've gotten professional pictures, drone, Matterport, and multiple walk-through videos circulating.

Obviously there is no guarantee but if someone with a high level of success and experience was willing to do all that, it is likely a go.Yes it is true there is seasonality in hospitality but with proper budgeting you will be fine.For estimates I personally use AirDNA (Paid version) and then double check it using enemy method.

Picture below is what it looked like when built in 1896.

Don't forget that Airbnb is sending messages, as well, so you will be doubling up.I have 3 auto messages:(1) Booked instantly - I let them know we are looking forward to their visit and highlight the unusual things about the listing that they might have overlooked about the listing and let them know they can cancel within 48 hours.(2) Morning after check-in - Asking them how their stay is and if there is anything they need.(3) 5:00 pm the evening before check-out reminding them of the check-out time and instructions.8 days before check-in, I send them a manual message reminding them of the upcoming booking and asking them for their ETA for an in-person check-in or instructions if they'd prefer a self-checkin.

Double Whammy).

The median home price has more than doubled in that timeframe, but Milwaukee is a fairly linear market, so the neighborhoods have mostly remained the same, but median home price is a dynamic indicator and will always stay current, so you can benchmark neighborhoods against the median for the metro area.Note: in the MF space investors refer to a star rating system. 1 star to 5 stars.

Question: Are there any investors turned real estate agents, living the "double life" and would recommend this?

Having two open loans for the property is not ideal as that's double closing costs but maybe that is a fairly normal strategy?

These are double wide homes that would be attached to the permanent foundation (on owned land, not in a park) and that the investor would look to sell right away to people that would occupy the homes as their primary residence. 

Most of the time in these situations these borrowers are high net worth and think big picture vs. counting the pennies.