Good Neighborhoods for STR :Champions Gate (17 min / 12 miles)Celebration (12 min / 6 miles)Windsor Hills (14 min / 5 miles)Kissimmee Area (Storey Lake) (26 min / 14 miles) - Not all communities allow STRDavenport (Town) (33 min / 18 miles) - Many communities in Davenport allow STR but not allSolara (22 mins / 13 miles)STR Not allowed in these neighborhoods (as of writing this post):Windermere (18 min / 10 miles)Harmony (17 min / 12 miles)Winter Gardens (26 min / 13 miles)Notes and Criteria:- there may be STR restrictions by Orange County so research before investing- Any property zone for STR is going to have an HOA that allows it.

As others mentioned, estimating software is only a means to quantity the work.  

Maybe it is a quality vs quantity situation.

Number of flips is the hard one: if you chase this number, you will be more focused on quantity vs quality.  

For the OP...everyone has a different quantity of deal flow required and value for their time.

Quality over quantity.

I would go with their mid-range window or their triple pane window, if you want their best for not that much more.Not sure if they have a minimum window order quantity these days as I used them about 4-5 years ago for a rental property where I replaced all the windows after purchase.

So refrain from paying for anything more than materials up front;  I even tend to have them letme know quantities of what they need, and pay for it myself and get it delivered to the site, so you're not giving them money that might just walk away never to be seen again. 

Whereas if everyone is on board to collect returns based on the actual building performance it aligns everyone a lot more harmoniously. 

You can find a lot of expensive tile at the $1 per sf range due to small quantities.