My properties are in Tampa, FL and the market there is pretty crazy right now. I've had these properties for 11 years and have never seen so many people looking for properties to buy and rent.

The rent I'm charging is $1400 for a 3B/2Ba sfh. Similar properties in this area are going for about $2000 now on Zillow and facebook marketplace, which is where I advertise (correct me if I'm wrong, zipcode: 33612). Even if I aimed for $1900, that's a 35% increase from current rent (43% if I raised to $2000). I have three properties that I can raise to market value right now, giving me an additional $20,000 per year minimum. That's no small amount. I am also painfully aware of how difficult it can be to find a great tenant. My current tenants are fantastic. Pay on time and take great care of the house, as if it were their own.

I'm so torn on what to do:
1. Place value in the current tenants being great, and raise rent minimally (if so, how much)?
2. Focus on the business, raise rent to current value and deal with the fall out of likely needing to find a new tenant? Will I find people who make the required amount to afford this? (Why wouldn't they own their own house if they make this much?)
3. Some kind of middle ground?

Secondary Question: One of the properties I can raise rent on is a 5 bedroom (plus office) property with a huge yard that is being used by the tenant as an AirBNB (yes, both me and the tenant are insured properly for this). They need to be able to make money from this property to make sense of renting from me, but they have taken the best care of the property I've ever seen. This neighborhood wasn't the best, so the people who would want to rent here in the past have not been the most ideal and I've spent tons in the past cleaning and fixing the property between tenants over the years. I feel like the neighborhood has improved some, but I still worry about whether I can find tenants to take good care of the house if I lost them. I could likely raise rent from $1700 to $2000, but not sure if it's worth it in this property in particular. It's in a different neighborhood than the other two.

Tampa, Florida

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