While it's exciting to cash in on a successful investment, the looming capital gains taxes can significantly cut into your profits.

This would be our first flip together, splitting cost and profit 50/50 with a hard money loan for what we cannot make up on our own.

Do you think Airbnb and VRBO consider your best interest and profitability when determining pricing, or are they just worried about getting guests into your place?

either by increasing direct profits or creating growth or both.

Can I still deduct all renovation costs from the profit in regards to paying taxes on the profit. 

If we're consistently profitable and find that the cleaner is not effective in responding to guest needs, then we will not hesitate to go the dedicated on-island agent route.

I've looked at the fastest growing areas in other states and while I think you can profit from real estate everywhere, perhaps with a different strategy, investing in the fastest growing areas in the state seems to me to give an edge or a push in the right direction.David KrulacBigger Pockets Podcast #82

Sold it recently to make a nice profit.

However, profits would be bigger if there were no HOA fee and there would be more opportunity to make improvements on the property.

If you have never done this as a full time business I will throw caution to the wind it is not as easy or as profitable as online forums make it out to be, and if you need money for living this probably is not going to sustain your lifestyle for the first several years.