Typically a few types of PMs out thereThe individual agent, little to no staffThe PM company that's a set it and forget it, glorified rent collectorThe PM company that's a true partnerI would on top of the suggestions abovesearch for a PM that owns their own portfolio tooThey treat your asset like they treat their own portfolio- There should be a full staff and readily available to answer the phone1.

My plan is to add 2 - 6 shipping container type of small houses and an above ground pool at some point to make at least a section of the property short/mid term rentals.

Meaning how to attract the type of people you want to your STR listings and how the heck you are supposed to know if there is a market for your type of "customer" in the area you are investing.

Do you have any advice on the best markets for this type of investment?

Here is a great resource. https://www.areavibes.com/They give you a total livability score and you can type any address in 

If you research recent sales you can always provide the appraiser a list of those sales.One of the best ways to insure a higher value is to update the property using materials and fixtures that are popular and common in the area.

Conventional 5% Down Loan (Owner-Occupied)If you live in the property for at least one year, you can use a primary residence loan with as little as 5% down.After a year, you can convert it to a short-term rental (STR).Loan types: Conventional (Fannie Mae, Freddie Mac)2.

Are you still looking for this type of deals?

Many lenders will just focus on your ability to pay them back in the time and allow you to 'lather, rinse, repeat' as much as possible, without the same type of underwriting procedures. 

@Vincent WeselakIt’s a good idea to get an estimate for your insurance costs upfront since this can vary based on the property type and location, and it’s a key factor in evaluating your cash flow.