I've only ever researched and looked in depth into STR but would be interested in expanding if the numbers of a MTR/LTR outweighed the benefits of a STR.Thanks in advance, everyone!

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.

But the appreciation you will see should outweigh any cash-flow you missed out on.

He weighs out the pros and cons of each action with you, and does not recommend expensive asset protection measures if the benefit doesn't out weigh the cost. 

pretty common reaction lol. the reality is that yes, investing does come with challenges. if you treat your investments like a business & really commit to being great at it, you will face far fewer challenges than the average mom and pop landlord. another reality of it is that the wealth-building power of RE, when done right, SERIOUSLY outweighs challenges like landlord/tenant issues. in life, find people who are doing what you want to be doing, and take advice from only them. block out the rest. 

Evaluate whether the potential benefits outweigh the higher costs and risks associated with hard money loans.

. I have seen situations where landlords and tenants are both very firm on their requested rent price and it was a minimal difference and the landlord let them move out and the money it cost the landlord to clean fix paint and rent the unit out to a new tenant outweighed the difference they would have made the tenant after moving expenses and paying first class and Security again probably outweighed what they would’ve paid had they just stayed so sometimes it’s better to just negotiate and flex a little to renew a tenant than to keep swapping tenants.

the answer i'm giving is based on the assumption that you do not want to / can not float the negative cashflow any longer. and note: even if appreciation / debt paydown / tax benefits strongly outweighed the negative cashflow, most investors wouldn't want to / couldn't float that. so that said, i say SELL. you have just over a million dollars in equity (minus transactional costs when you sell), and you could do a 1031 exchange into a ~4 million dollar CASHFLOWING property. i invest long distance into value-add multifamily on the west side of chicago. gearing up for my next deal right now. in that price range you could easily get a value-add multifamily with potential to cashflow 15k/mo+++ (up to 40k/mo) once it reaches its full potential. it sounds like you're in markets that are probably strong for appreciation and weak for cashflow (with the long term rental strategy). if cashflow is your goal, 1031 into value-add multifamily in a higher-cashflow area. don't let having to pay commissions during the sale stop you. you're already losing so much annually; you have to stop the bleeding at some point. also note that right now, with the way these two properties are losing money, that might negatively affect your borrowing power when you go to buy the family home. feel free to dm me if i can help in any way!

However, it ultimately depends on your risk tolerance and whether you believe the benefits of asset protection through an LLC outweigh the potential risks.

In my experience, the risk and headache of doing a custom rehab outweighs the benefits.The obvious benefit is that you already have a buyer and you might get more money.