To answer the first big question in your post — single family vs multi-family — I am firmly in the multi-family camp.

Here are some important questions to ask when choosing a specialist.Does the firm have engineering licenses with the state authorities?

To thrive in real estate investing, you must maintain a firm grip on your finances.

But if you have a cash buyer who is specifically looking for income property, and even more specifically a vacation rental property,  I firmly believe that there is a value add from having a working STR there.

Be firm and follow the law, don't let her fall further behind. 

If  you build your foundation in anything in life illegally is it a firm foundation?

@Christopher Morris, after being an REI myself since 2019 and our bookkeeping firm serving many REIs who have different strategies/business models, I'll tell you what is super clear to me...Never rely on rental properties to feed your family.

If it is later found to be the work was not performed according to code or properly repaired, we will seek damages from your firm since you knowingly hid this from us and would not allow us to understand the extent of the damage which occurred behind walls.Thank youThis way you are putting them on notice that you were aware damage occurred and they did not allow you to properly inspect it.

To thrive in real estate investing, you must maintain a firm grip on your finances.

If you haven’t already, make sure you’ve documented everything thoroughly—photos, messages, invoices—and highlight the guest’s negligence, like leaving windows and doors open in extreme weather.If you haven’t heard back after asking to escalate, follow up again and politely but firmly request that a senior claims specialist review the case.