It sounds like you have a solid plan in place, and I'll provide some insights and advice based on your questions:Maximizing Investment Longevity:It's a smart move that you're house hacking with an FHA 203K loan, remodeling for appreciation, and then refinancing to extract equity for other investments.

So they provided much more value than they got in commissions in my experience and set me up for success in my investing career.

Your cleaner may have had a whole team there working on the house, especially for a conversion from residential to STR.bottom line, the rate is not unreasonable if a deep clean was provided and done correctly. 

High Maintenance Costs: Escalating maintenance costs can erode your profit margins.Change in Neighborhood Dynamics: Shifts in the neighborhood that negatively affect your property’s value are a red flag.Better Investment Opportunities: Selling might be wise if you've identified a more lucrative investment opportunity.Cash Flow Necessities: If you need liquidity, selling a property can provide a significant cash inflow.Tax Implications: Sometimes, selling can be advantageous for tax reasons, especially if you can benefit from capital gains tax laws.Personal Financial Changes: Changes in your personal financial situation may necessitate liquidating assets.Retirement Planning: Selling investment properties can be part of transitioning into retirement.Portfolio Diversification: Selling might be necessary to avoid overconcentration in real estate.Legal or Regulatory Changes: New laws or regulations can impact the attractiveness of holding onto a property.Ownership Challenges: If the burden of ownership outweighs the benefits, it may be time to sell.Real Estate Market Trends: Anticipating a downturn in the market can be a reason to sell early.Interest Rates: Rising interest rates can reduce the pool of potential buyers and lower property values.Property Value Appreciation: If your property has appreciated significantly, taking profits might be smart.Lifestyle Changes: Sometimes, personal life changes dictate a shift in investment strategies.ConclusionDeciding to sell an investment property is a complex decision influenced by market conditions, personal circumstances, and future investment goals.

We're also able to evaluate our rates, and keep pace with inflation, on a monthly and quarterly basis because of shorter term leases.These syndication can provide an 8%+ cash-on-cash return - providing you monthly cash flow - and a 15-20% IRR over the length of the project.

If this is your first rental property - I'd also recommend an agent that can ensure you are looking at the right kind of home, area, and type to ensure it meets your financial objectives and provides you with a return.I've been an investor in Charlotte for over 10 years and also host a meetup called "SouthEast Charlotte Real Estate Investors/FI" - find us on FB.

I went so far as to discuss options with different providers in the NYC area.

I'm a trust but verify guy so 3 times a year we have picture inspection reports done so I know the condition of the unit, cost $75, Will share information if requested.Best,Mike Money well spent.In think we do a yearly walkthrough that is included with our PM operation but would like to have multiple walkthrough's scheduled every year which we will probably have to charge for due to needed time and resources.But it's a great way to get eyes on the property and provide peace of mind for landlords.Thanks for the mention.

Actually go through it with them, make sure they understand what they're providing and what you're providing. 

You could add a ductless minisplit system that would provide air conditioning and also heat.