Milk Junkies is a rad website/blog about parenting and breast/chestfeeding from a transgender perspective!
Here is a simplified list of tips from Trevor, a trans*parent who has successfully chestfed.
For the complete post, with all the helpful details, click the link provided in this post!
Tip One: Simply know it is possible.
Tip Two: Know that latching will be particularly tough.
Tip Three: Be aware that in the case of a trans guy who has not had any chest surgery he may have practiced years of breast binding to flatten his chest, and this, of course, may affect milk production.
Tip Four: Watch out for postpartum depression even more than usual. Feelings of guilt, body discomfort, or gender discomfort may arise and need to be addressed.
Tip Five: Trans*parents may find it helpful to have allies act as a go between when setting up with groups such as La Leche League. It can be intimidating for a cis*parent to attend these groups or meetings, and even more intimidating for a trans*parent.
A final word from Trevor: Be prepared to learn, innovate, and improvise. Have fun!