Potential Condo as 1st Investment Property

[Antonio Chase]

I'm new to real estate investing. I'm looking to make my first purchase of a condo in what many consider a desirable area in Tampa Bay. This is not new construction but the condo is relatively modern by today's standards and as mentioned earlier, it's in a rather tony area. The unit's deed will be transferred to an LLC. I read in the HOA rules that any unit owned by a business must apprise the Board of the name of the person(s) occupying the unit. Further, the name of the person(s) occupying the unit cannot be changed more than once every 6 months. I'd planned to use VRBO in lieu of LTR. Also, I believe the LTR rate may not cover the costs including maintenance/repairs. If I were to go the VRBO route, I wanted to have a minimum stay of 30 days. Now, it appears the minimum stay is 6 months based on this HOA's rules... Questions. 1. Can you share your experience with VRBO, if used as a rental option, in obtaining renters willing to commit to a 30-day rental? To a 6-month rental? 2. Is there a free tool you can recommend that I use to help determine if an investment makes sense? Also, I open to learning about alternatives to VRBO that is not AirBNB. Thank you for advice and experiences.