I started working out a little and my left shoulder started giving me problems and I basically quit.  

So you will work on your credit while learning to underwrite deals. 

•Are the listing photos working against you?

For example, we do a lot of work within Philadelphia and Pennsylvania (both have different standards regarding legal/safe lead-levels).

Speaking from hands on experience on both platforms as I've worked with both Carrot and Wordpress sites (more than 400 sites so far since 2017), what carrot brings into the table is their simple, all in one, fast website platform.

Things like this are why it's important to work with a professional who is well versed in real estate taxation because the "common/simple" strategies taught frequently like BRRR or house hacking actually get fairly complicated when it comes to handling it correctly. 

I had no idea who we were working with as I was lead to believe it was one of his clients from his tax business.

The property has to be considered 'in service' for you to list it on your tax return.In service entails a couple of items such as1) The property is in livable condition - Working bathroom, kitchen and an area to live.2) The property was advertised for rent.Best of luck

The homes don't have MLS sale history until they are listed after the rehab has been completed.If you don’t mind shaing, how are you financing your deals and do you do the work yourself?

I can tell you with confidence that Many of my clients have done both and it worked out.