Hi Charlie - I am a huge believer in managing the properties yourself if it fits with your goals. This is especially so at the beginning when you may have fewer properties and will benefit greatly from having seen "under the skirt" of property managing so that if you ever decide to turn your management over to a "professional" you will know what you should expect and what you won't tolerate.
If you are just starting out with a few units, I would use an excel spreadsheet or quick books which will force you to learn what goes where. As you get bigger, having done this will help you choose a software program that works for you. I like Appfolio but it does have some missing pieces.
There is a lot to know to really have your property management run smoothly. If I were just starting out with a manageable number of properties here is what I would do:
1. Join my local rental owners association. Hopefully you will find one that can make the locally approved forms (applications, leases, pet agreements etc.,) available to you for a small fee. Use these while you are getting started to be sure you are in compliance. Don't just grab any old form off the Internet. As you become more experienced, you can add additional provisions to your new leases if you find it necessary.
2. If your local association offers a resource that compiles the applicable landlord/tenant laws and acceptable forms -buy it and make yourself and your wife VERY familiar with the rules on accepting and responding to applications, having written screening criteria, taking/holding/and refunding security deposits, move in checklists (don't get slack in this), and fair housing. Always assume you are talking to an undercover housing authority person when you are interacting with tenants. This is where your screening guidelines come in. If you have the right guidelines and follow them you will have nothing to worry about and will by and large get good tenants. It is absolutely worth it to educate yourself up front on these rules so you aren't at the mercy of a career tenant and can feel good about the decisions you will make along the way.
3. Choose your tenants wisely and never fail to screen. I make a point to meet any tenant I am seriously thinking of renting to but then again I am still small enough to do this. When i am buying properties for rentals I am always asking myself "what kind of person will want to live here?". If the best that I can realistically hope for is not a person I want to work with I pass on the property. I also strive to keep my properties well maintained, safe, and clean in the hopes of getting the best tenant I can.
4. Pay very close attention and develop skills for lightening fast (that is the goal) turnovers. One of the things you learn while managing for yourself is just how costly turnovers can be. VACANCIES WILL KILL YOUR PROFITS AND CASH FLOW!!!! Get really good at getting into units you know will be turning over ahead of time so you are prepared for all the maintenance items and have them scheduled for the moment the unit is vacant. Solidify your renewals early and if you anticipate a vacancy or know you have one coming, get your ads up quickly and talk to your tenants about clusters of time when you can show the unit. I incentivize my current tenants to cooperate with showings and keep the units looking nice for showings by offering them a gift card or cash when I get a tenant through a showing.
5. Set your rules and gently but firmly enforce them.
6. Spend the time at check-in to do a thorough job of documenting the condition of the unit. Hopefully you have delivered it to them in a condition that will represent how you hope to receive it back. Your rights to reimbursement for any damage is based on your documenting at move-in.
7. Spend the time at check out to make your tenant aware ahead of time exactly how you expect the unit to be returned to you and even add a sheet indicating a range of what it will cost for each item left undone (there is a really good one in forms section here at BP).
8. My rent is due on the 1st and a late fee is incurred if not paid by the 5th. On the 3rd or 4th, if I have not received rent from someone, I send them a text (my tenants all agree to be contacted this way) that says " Hi tenant, this is a friendly reminder that I have not yet received your rent. If I don't have it by the 5th a $75 late fee will be added to your account." I don't get tenants that pay late (past the grace period) but if I did, I would post a notice immediately so they know I'm serious and follow through if it didn't get cleared up.
8. Be fair. Get good tenants. Keep your places maintained. Move quickly to deal with anyone that is breaking the rules or not paying.