So eventually this negative cash flow property becomes cash flow positive and pays for itself including property taxes, hoa, mortgage etc.Trying to calculate how bad is my investment here or should i sell out if there is appreciation 

If not, I have included an article below that sheds light. 

I have been digesting all things Real Estate so right now I am working to lower my DTI while saving at least 6-7% for the Owner Occupant down payment (to include closing cost, etc.).

However- as the land around them develops, the house will become worth less on the retail side, but at some point, a developer will come in and pay way more than the retail value in order to include their parcel in a larger development.

As a short-term rental property manager in Massachusetts, I charge a 20% co-hosting fee, which includes full-service management—guest communication, vendor coordination, cleaner oversight, and overall property operations.I've seen competitors charge anywhere from 10% to 30%, but lower-cost managers often cut corners, while higher-end services may not always justify the price.

Common fees will include a set-up fee, a leasing fee for each turnover or a lease renewal fee, marking up maintenance, retaining late fees, and more.

My team and I are also out-of-state investors, including a managing partner who was born and raised in Toronto.We’ve been investing in Cleveland for a little over a year now and currently own 22 units in the area.

My target market is South Florida, including Miami-Dade County, Broward County, Palm Beach County, and possibly Collier and Lee Counties.

We have also negotiated attractive loan structures with many lenders including reduced fees for our community, free refinancing, lower rates, unique portfolio options, etc.

There are certainly some things to learn along the way, but you'll figure it out as you go just like we all do.There are plenty of folks here that would be happy to help for free - including me.