Personally, I would go directly for the 5516-X which is only slightly more expensive but much faster with FirePower.
Does the filter block HTTPS requests?
It's possible to configure SSL-policies where you define which traffic to decrypt and which to drop or pass without decryption.
Does the filter work well, is consistent with blocking sites?
FirePower uses the Brightcloud URL-database. I think it's of high quality although some of the classifications are a little strange. They react quite fast on reports for wrong classifications.
Is it difficult to set up through the ASDM?
I would say yes. The system is extremly powerful and has many options. You have endless possibilities to misconfigure something. Take some time to get used to the system and/or attend a training-class on Firepower. In addition to tat I would not manage FirePower through ASDM. If you have VMware, use FirePower Management-Center.
Alternatively you could look into the Meraki MX84. By far not that many options to configure, but with limited manpower you probably get better security as with a FirePower system that is not optimally configured.