Quote from @Chris Shon:We started an LLC last year and are about to file our first return for 2024.

Last 2 years single family has continued to increase due to limited supply even as rates are where they are (which is not actually high).

Capital gains are calculated as:Sale Price - (Original Purchase Price + Capital Improvements + Selling Costs) - depreciation (if applicable) = Capital GainYour mortgage or HELOC balance does not affect this calculation—it only determines how much cash you take home after the sale.In Massachusetts, if the home was your primary residence for at least 2 out of the last 5 years, you may qualify for the Section 121 Exclusion, allowing you to exclude up to $250,000 (single) or $500,000 (married filing jointly) of the gain from federal capital gains tax.

I spent the last almost 3 years doing my due diligence learning the lay of the land.

We bought a 55-unit last year in the same market, a market we've been investing in for seven years.How we found itOur property manager brought us this opportunity (and the three previous as well).

I have purchased 3 STRs personally in the last 18 months and have closed on at least 25 for clients in the past 12 months.  

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

I made a fair size claim last year and it paid off pretty painlessly except for the 90 day lag. highly recommend them.If I had used a regular home owners policy with and STR addendum I'm pretty sure it would not have covered my particular issue.

That was an excellent non-answer to my question, Skyler. hihi :)No they are not all the same. some are only interested in dealing with conventional purchases other are as you say better at handling assignments or double closes, some are commercial specialty, etc....A investor friendly one would be, at least from my point of view, one that understands there may need to be some last minute wheeling, dealing, and adjustment made to close a deal, understand what needs to be done and do not freak out about creative deals.Maybe my understanding or thoughts are wrong but that's what I meant by investor friendlyregards :) 

They pointed out all the things the last company did wrong, and gave me a quote for $4000.