@John Montgomery Congrats on getting close to negotiating your first deal...I would say the most important thing is to "know your objective"...There are a lot of great answers on this thread, but ultimately we are all making "shots in the dark" as to the best option for you because it's our perspective...This is still valuable, but can become very confusing because you don't know each person's perspective...MY Suggestion is to know your goal over the next 3-5 years...I will let you know a little about my perspective...I am a Rehabber and Have Been Buying and Rehabbing over the past 8 years here in Chicago...I've been in your shoes...I wanted to be the Big Shot and rehab deals straight out the gate(Little to No Money & No Experience but a few REI Boot Camps- basically No Experience)...To say I've had a lot of Failures during my 14 years of being involved in studying REI is an Understatement...If I was starting all over again, and my objective is to be able to build a robust REI Biz that can allow me to rehab 6-12 homes a year, wholesale 2-3 properties per month, and build a rental portfolio...I would first focus on getting good at one objective first...Generally most people start out wholesaling because it doesn't require the money or experience rehabbing or landlording requires...I would start with Wholesaling...go find 5-10 very good rehabbers and find out their Criteria for a Great Deal...Commit to building Value for them and ultimately a great relationship.With this you will already have buyers lined up, you know what areas to look for properties in, and you can research public record and see what they are paying for properties on the acquisition(and also ask them, but keep them honest by researching public record)...At this point become the best wholesaler to these rehabbers...you will learn a lot just in this process alone...How to evaluate Comps, Repair Values, Neighborhoods, etc...Which a great wholesaler will know how to do...It will make your deals easier to sell...Ultimately I would see which one of these Rehabber will be open to the idea of partnering/mentoring me on how to get into that arena...They may even allow you to follow the progress of their deals...Every deal has its surprises and over the course of 10-20 deals you will get a real life idea of what those surprises are, and even understand the "reason why" you calculate certain contingencies into deals and also what are the most costly mistakes or repairs to look for and avoid on deals...The value of this Experience will accelerate your learning curve...In my experience one mistake for a beginner can cost you a ton of money and even put you out of the rehab business.There is no way you can learn all the mistakes you must avoid by reading a book or taking a 3-day training program. 

Your tenant knows he has a good deal and will not be surprised that you are raising the rent {he may outwardly act otherwise}.We took over a triplex a couple of years ago where the long term tenants in one unit had not see a rise in rent in over eight years.  

I am a little surprised sometimes by what people think is okay.

Things happen unexpectedly and the 86$ dollars you would be receiving is not going to go very far.

I was pleasantly surprised.

And don't be surprised if they change the loan a day or two before closing.

It is my first offer so I'm surprised.  

Right now, it does not surprise me when the seller tells me they have 20-30 people coming out to look at the property.

So, this nice couple thought that the bank has already taken over the property and were surprised to learn that Citi has not even filed a foreclosure action yet.

I bought in october 2013 and the tenants only came in february 2014, I had unexpected high maintenance cost and excessive Bill from the attorney.