Being that you already have property management experience and feel confident in your ability to manage a single-family or multifamily property, it really comes down to your financial position.If you have a good amount of cash available to put a down payment towards the purchase of a property and maintain sufficient cash reserves (or if you have a partner you can work with who does), then there's nothing wrong starting off with a multifamily property. 

As long as you and your CPA maintain thorough and accurate records, you should be in good shape.

If you're going to keep it a rental, you want to "maintain to the neighborhood", NOT your personal preferences (or that of your siblings).What's the estimated cost of any required repairs?

They prevent bedbugs from entering or escaping mattresses.Routine Inspections: Regularly check mattresses, bed frames, and furniture for signs of bedbugs (small black spots, eggs, or live bugs).Furniture Choice: Choose furniture with metal or plastic legs instead of wood, as bedbugs are less likely to infest non-porous surfaces.Bedbug Traps: Place bedbug traps under bedposts and other furniture legs to catch any potential bedbugs before they become a problem.Professional Cleaning: Schedule routine deep cleans between guest stays, and if you ever suspect bedbugs, hire a pest control professional immediately.Clear Guidelines: Educate your cleaning staff on how to spot bedbugs early, and encourage them to report any signs immediately.These steps will help you set up a smooth, well-managed STR that’s ready to generate revenue while maintaining a good relationship with your LTR tenants.

How do you find contacts, reach out, market and then maintain your relationship with them?

Most prospective guests can indeed see through an overly picky critique.However, there are ways to respond to critical reviews that maintain professionalism and avoid coming off as defensive:Keep it Short and Professional: A brief, polite response shows that you care without getting into the details.

The reason behind that is simple: maintaining infrastructure for low density single family housing is cost prohibitive. 

Present yourself as the profesional with high end software and should help to maintain your growth going forward.

Tenant risk is lease term remaining, sales/billings from the location, overall financial health of the tenant (i.e. solo practitioner with this one center as their sole source of income and declining billings, will not likely keep the property well maintained, and when they move out, you will have work to do), need for this use and/or competitive urgent cares in area, etc. 

The important points often glossed over are (1) is the buyer providing their personal guarantee to the seller for the note (2) is the seller maintaining a wrap position so they can foreclose in the event of default and gain ownership (3) is the buyer putting up additional collateral (4) how large is the down payment (5) what is the LTV (6) is this a personal residence for the seller or investment property (7) will the property cash flow and if so what will the cash flow be (8) is the property in a increasing, declining, or stabilized area (9) is the property being sold at market value, or above market value because of the low interest rate of the existing mortgage and (10) how experienced and what is the track record of the buyer, and is the buyer purchasing a property for investment or to live in or otherwise use.