The new condo in Hawaii needs a lot of work and I plan to move in while making the improvements.

Some renters might want to see some kind of improvement or reason for the rent being raised or they could end up leaving.

I let the tenants pay down my mortgages and I use my cash flow to buy more properties or to improve them in a way that increases my NOI. 

I have allocated 3 months to this flip and obviously sooner is better, but that is what was budgeted (feel free to give advice on how to improve my timeline).

That's a standard approach for many county roads, and is well-known for lower cost and durability.As long as you are trying to improve the roads, don't forget to install paved "parking pads" -- typically 20' x 20' squares to park two cars on each lot.

In my experience flippers make the quality of a city improve, but like @Greg H. said, there is the "you aren't from around here" factor at play.

If you purchased a property, significantly rehabbed the property and immediately sold it thereafter with the intent of flipping it, it will be subject to self-employment taxes.Regarding the taxes you will be subject toFederal TaxesState taxesDepending if it was a flip or not, also self-employment taxes.Speak with your accountant on the actual taxes that will be due as he/she will know what your marginal tax rates are.You can also factor in improvements / selling costs to decrease your gain / taxes.

How to Win Friends and Influence People - Dale CarnegieIf you read and apply the lessons of this book your networking & communication skills in improve significantly.Example: I met one of my best clients years ago and we were recently talking about the day we met.

I read more & thought more after my post and could likely avoid capital gains all together since I lived in the hole most of the past 5 years and make less than $500k when filling married jointly - this making me eligible for the personal residence exemption.

We immediately did a cosmetic rehab on the property and over the years have made cosmetic improvements.