You'll raise red flags if you claim you're buying a second home and it's a condo downtown which is 10 miles from your primary residence.

3 homes on the same block, 2 of which are neighboring have gone on the market in my farm area within 2 weeks of each other.  They are priced moderately based on comparable.  I personally find this a bit suspicious but...

Some carriers also don't want to insure more than a certain number of properties, or only allow so many investment properties. you just need to reach out to insurance brokers, or insurance companies that cater to investors.

Meters were turned off and to get those meters turned on you will need anything from a great set of plans, From electricians to Plumbers, to framers, etc.4- Sometimes the city will make the new build have up to date codes for electrical and access to building with complete inside sprinkling system .5-10   I could go on and on but I think you are getting the picture.Have your Real Estate agent call the city planning permit division and see what "Red Flags " are on the property address.If there was lose of life,  it will be very difficult to do a simple Re Hab on this property without the city making it up to every code in the book!

I have seen highly experienced professionals do simple work and get something minor flagged during inspection.

When looking for a motivated seller that has a property that falls under the definition of a "good deal", what are red flags I should look out for before getting their property under contract?

When someone starts their tenancy with assistance from another source, that's a red flag that should be watched closely.

The fact that none of them has a credit card is a big flag that they probably aren't financially mature enough to navigate this kind of venture.

Also, this would be my first 'package deal' purchase so if there are any tips or red flags to look out for, I'd greatly appreciate it!

In the event that some red flags pop up during the inspection then you can either negotiate with the seller to cover the costs or terminate the deal and move onto the next one.