First just want to state, she is your girlfriend not your wife, which is very different in regards to financial status/situation.For me its simple, I am buying this asset and taking on the risk of renovating it and as part of it will be seeking to earn income from it to better myself in the future as I know a W2 job and a 401k does not get you far in retirement.

We had him as a guest on our podcast - the DC Real Estate Podcast, he was episode #10 yea with half million dollar homes you can buy 10/15 properties in the D that will net double then DC 

Here is what I proposed:Setup fees : Administration Setup:One Time Fee: $400Guidebook: Using professional photos give the guests a professional tour of the house and how the home works (Wifi passwords // How to use grill // How to use propane fireplace // Hot tub instructions // Sauna instructions //Check in and check out instructions //where extras may be storedOTA (Online Travel Agency) setups: taking professional photos and actively updating your listing on popular platforms;PMS (Property Management System) Setup Smart Pricing Set upWebsite integrationOther (furniture arrangement / design / décor shopping and set up) $50 per hour· Placement fees · Marketing Cost: Variable depending on needs/wants for marketingFacebook AdsGoogle Ads Cleaners: Set up procedures/take pics of expectations· Management fee—30%Guest communicationCleaner communicationSetting Rental rateDealing with small maintenance issuesBooking CoordinationSmart Lock integrationKeeping supplies stocked (TP, paper towel, all cleaning products, coffee, filters, creamer, sugars, teas,)(Receipts would be submitted on a monthly basis for either reimbursement or book keeping purposes)Encouraging guests to leave good reviews by periodically checking in, providing a review template, and ensuring guests receive the amenities they are looking forContinued marketingMajor Maintenance fees—OwnerCleaning and laundry services fees: Cleaning fee to the guest depending on how cleaner wants to charge

Milwaukee is very often misunderstood; what looks great online and on paper (super low price, high cash flow) is usually fools gold in the form of a 100 year old hours that needs everything new, the poorest neighborhood, and high maintenance tenants.

Shiloh Lundahl -  Man this is gold. 

I figure that everyone has a cellphone these days and if a guest drops by then they can simply call the tenant when they have arrived to be let in.

I am not sure what the status of it currently is — already capped, I imagine.So based on my current circumstances, and in alignment with your suggestion, I was thinking that the best option would be for me to continue to live in this condo, continue saving up, and then combine my savings + pull equity from this prop to invest in an affordable investment property when I can, ideally after a year or so.

As for the value-add, I would manage all guest communications, pricing, listing, and other daily responsibilities, while also having a on-site team for all properties.

Guests book our cart through the platform and Fenderly handles the security deposit and everything else. 

You need to reach out and get update on status.