You can add the per booking charge as a resort fee to each booking, then the guest is paying for the coverage not you.

I live near Baltimore, MD but I’m from Upstate NY originally.

Also a (PM) lender should not charge you a fee to apply for a loan.

.- Property now rented for $1000 per mth- Current Value Estimates: Redfin - $114K, Trulia - $113K, Zillow: $113K; still doing research on comps because the area is hit and miss so last I saw was a projected $100K***************************************************************************************************************************- Navy Federal Credit Union say they can do 65% of original purchase price in cash out refinance - $34K- Hard-money lender offered $30K at 9.9% for 6 months as rehab loan, which I'd use to replace roof, windows, doors, and cutdown at few trees;  then cashout refi for 50% of the appraised value between 6 and 9 % depending on personal credit.

When preparing tax returns, my fee difference between landlords who bring me a spreadsheet and landlords who bring me a shoebox full of receipts is significant.

Also, it goes without saying that you should consult an attorney; Okay briefly reading over your lease agreement, it's a good agreement but it is very loosely written and does not provide for many remedies prior to eviction so... that is something you should look to improve on moving forward, there should be an escalation of force in as $XX fee until rectafied and THEN otherwise eviction, also you should number your lease clauses.Regarding the current situation first and formost, I understand you live in the property as well but you should certainly take on a 'HANDS OFF' approach in regards to internal disputes amongst Tenants; you are after all a landlord, not the ethics police nor the real police.... if other Tenants have issues such as those they should inform you and then they should contact the police... if it's not police worthy than it is more than likely just internal bickering. 

If it needs to be bought at 40K to make sense then offer below to cover your wholesale fee

What I did was to add special incentives including no pet fee and a discount on a golf cart fee.

Make sure you document your original cost so you can show the loss on your taxes. :-). 

You get that back if you sell, but if you keep it as a rental it takes 153 months or 5 years to break even on your down payment alone.https://www.redfin.com/IN/Indianapolis/1515-E-Kessler-Blvd-Dr-46220/home/66981054ARV / Sell Price$235,000We Calculate All CostsPurchase Price$152,750 65%Closing Costs$2,000Rehab$30,0006 Months Carrying Costs$9,114Real Estate Selling Costs$14,1006%Other$0Other$0Total Rehab Costs$207,964Now We Calculate ProfitARV / Sell Price$235,000Total Rehab Costs$207,964Gross Profit$27,036IRS Tax$4,05515%Net Profit$22,981Per month profit$3,8306Loan Down Payment$30,55020%Loan Amount$122,200 80%Loan Cost per rmonthPrincipal & Interest$8137%Prop Taxes$321Insurance$168HOA Fees$0Monthly Payment Costs$1,302Monthly Payment 1$1,302Monthly Payment 2$1,302Monthly Payment 3$1,302Monthly Payment 4$1,302Monthly Payment 5$1,302Monthly Payment 6$1,302Utilities for 6 months$1,302Total for 6 Months$9,114