There are different SMD systems:
SOIC - Fairly easy to solder using a broad tip, faster than DIL (8 pins to 28 pins)
TQFP - you need flux and desoldering pump or reflow, TQFP44 is easy
leadless QFP, ball grid (BGA) - pick'n'place machine, not designed for manual mounting
TSSOP (0.5 or 0.4mm pitch) - can be soldered manually if need be I would only recommend for prototype
It is possible to do it manually but the part must become aligned nearly 100% or it's very difficult to take out
the extra solder using row soldering.
If you already have DIL based design use adapter PCBs? There is different pricing,
if you produce them yourself they cost a dollar or less
DIL packaging also is quite bulky compared to SOIC or TQFP (thinking of the waste).
You don't need special soldering tip or extra tin soldering wire.
Reflow depends if you do it professionally for instance use a printer for the solder paste,
a stencil or if you apply it manually. I have good success with small SOT23 (6 lead) parts,
they need rework but the placing is correct using "homegrown" reflow. And I use lead-based
solder for rework the surface tension seems to be higher.
SOIC also aligns correct but always needs rework. Using a broad tip it's fairly easy to pull solder
ball along the pins you don't even need flux.
Maybe you don't want to redesign boards completely to SMD, using adapter PCB might be an option.